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PiHKAL

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From Wikipedia, the free encyclopedia

1991 book by Alexander Shulgin and Ann Shulgin

Not to be confused withPikal.

PiHKAL: A Chemical Love Story
Cover ofPiHKAL, 1st ed.
Author	Alexander andAnn Shulgin
Subject	Pharmacology,Autobiography,Psychoactive drugs
Publisher	Transform Press
Publication date	1991
Publication place	United States
Media type	Paperback
ISBN	0-9630096-0-5
OCLC	269100404
Followed by	TiHKAL (1997)

PiHKAL: A Chemical Love Story, also known asPhenethylamines I Have Known and Loved, is abook byAlexander Shulgin andAnn Shulgin published in 1991.^[1]^[2]^[3] The subject of the work ispsychoactive phenethylamine chemical derivatives, notably those that act aspsychedelics and/orentactogens.^[2]^[3] The book has two halves, with the second part containing detailed entries on 179 phenethylamines.^[2]^[3]PiHKAL was followed byTiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).^[4]^[5]

Content

[edit]

The book is arranged into two parts, the first part being a fictionalizedautobiography of the couple and the second part describing 179 different psychedelic compounds (most of which Shulgin discovered himself), including detailedsynthesis instructions,bioassays, doses,durations, and other commentary.^[2]^[3]

The second part was made freely available by Shulgin onErowid while the first part is available only in the printed text. While the reactions described are beyond the ability of people with a basic chemistry education, some tend to emphasize techniques that do not require difficult-to-obtain chemicals.^[3] Notable among these are the use ofmercury-aluminium amalgam (an unusual but easy to obtainreagent) as areducing agent and detailed suggestions on legal plant sources of important drug precursors such assafrole.^[3]

Members of Shulgin's research who contributed to the experience reports included Shulgin himself,Ann Shulgin,Myron Stolaroff, and Jean Stolaroff, among others.^[6]^[7]

Response

[edit]

ThroughPiHKAL (and laterTiHKAL), Shulgin sought to ensure that his discoveries would escape the limits of professional research labs and find their way to the public, a goal consistent with his stated beliefs thatpsychedelic drugs can be valuable tools for self-exploration. TheMDMA ("ecstasy") synthesis published inPiHKAL remains one of the most commonclandestine methods of its manufacture to this day. Many countries have banned the major substances for which this book gives directions for synthesis, such as2C-B,2C-T-2, and2C-T-7.^[8]

In 1994, two years afterPiHKAL was published, theDrug Enforcement Administration (DEA) raided Shulgin's laboratory and requested that he surrender his DEA license. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated in reference toPiHKAL "It is our opinion that those books are pretty much cookbooks on how to make illegal drugs. Agents tell me that in clandestine labs that they have raided, they have found copies of those books", suggesting that the publication ofPiHKAL and the termination of Shulgin's license may have been related.^[9]

Notable compounds

[edit]

Some compounds inPiHKAL, likemescaline,DOM,2C-B,MDA, andMDMA, are widely known and/or usedpsychedelics and/orentactogens.^[3]

Essential amphetamines

[edit]

The "Essential Amphetamines" are what Shulgin describes as ten amphetamines that differ from natural products such assafrole ormyristicin by an amine group (PiHKAL Entry #157 TMA).^[3] The list consists of:^[3]

PMA (para-methoxy-amphetamine)
2,4-DMA (2,4-dimethoxy-amphetamine)
3,4-DMA (3,4-dimethoxy-amphetamine)
MDA (3,4-methylenedioxy-amphetamine)
MMDA (3-methoxy-4,5-methylendioxy-amphetamine)
MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine)
MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine)
TMA (3,4,5-trimethoxyamphetamine)
TMA-2 (2,4,5-trimethoxyamphetamine)
DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine)
DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine)
TeMA (2,3,4,5-tetramethoxyamphetamine)

Not all of these chemicals are bioassayed inPiHKAL; some are merely mentioned.^[3]

Magical half-dozen

[edit]

The so-called "magical half-dozen" refers to Shulgin's self-rated most important phenethylamine compounds, all of which except mescaline he developed and synthesized himself.^[3] They are found within the first book ofPiHKAL, and are as follows:^[3]

2C-B (2,5-dimethoxy-4-bromophenethylamine)
2C-E (2,5-dimethoxy-4-ethylphenethylamine)
2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine)
2C-T-7 (2,5-dimethoxy-4-propylthiophenethylamine)
DOM (2,5-dimethoxy-4-methylamphetamine), DOM being short fordesoxymethyl, referring to the removal of the oxygen atom from the methoxy group on the "4" carbon.
Mescaline (3,4,5-trimethoxyphenethylamine)

All six are now Schedule I controlled substances in the United States.^[10]

Ten classic ladies

[edit]

Shulgin systematically replaced the 10 uniquehydrogen atoms in DOM withmethyl groups in order to explore its activity and named these compounds the 10 classic ladies.^[11]^[3] The resulting compounds were as follows:^[11]^[3]

Ariadne (α-ethyl-DOM)
Beatrice (N-methyl-DOM)
Charmian (α-methyl-DOM)
Daphne (threo-β-methyl-DOM)
Elvira (erythro-β-methyl-DOM)
Florence (2-desmethoxy-2-ethoxy-DOM; DOM-2ETO)
Ganesha (3-methyl-DOM)
Hecate (DOET; 4-desmethyl-4-ethyl-DOM)
Iris (5-desmethoxy-5-ethoxy-DOM; DOM-5ETO)
Juno (6-methyl-DOM)

As with the essential amphetamines, not all of these compounds have been bioassayed.^[3]

Some additional "ladies" have also since been named, includingJulia (DOTMA; 3,6-dimethyl-DOM),Jelena (2C-IP), andSelene (2C-P).^[11]^[12]

Phenethylamines listed

[edit]

#	Substance	Chemical name	Group	Dose^a	Duration	Link
1	AEM (α-ethylmescaline)	α-Ethyl-3,4,5-trimethoxy-PEA	4C-scaline	>220 mg	Unknown	[1]
2	AL (allylescaline)	4-Allyloxy-3,5-dimethoxy-PEA	Scaline	20–35 mg	8–12 hours	[2]
3	ALEPH (DOT, para-DOT)	4-Methylthio-2,5-dimethoxy-A	DOx	5–10 mg	6–8 hours	[3]
4	ALEPH-2	4-Ethylthio-2,5-dimethoxy-A	DOx	4–8 mg	8–16 hours	[4]
5	ALEPH-4	4-Isopropylthio-2,5-dimethoxy-A	DOx	7–12 mg	12–20 hours	[5]
6	ALEPH-6	4-Phenylthio-2,5-dimethoxy-A	DOx	>40 mg	"Probably long"	[6]
7	ALEPH-7	4-Propylthio-2,5-dimethoxy-A	DOx	4–7 mg	15–30 hours	[7]
8	ARIADNE (4C-D; Dimoxamine)	2,5-Dimethoxy-α-ethyl-4-methyl-PEA	4C	Unknown^b	Short	[8]
9	ASB (asymbescaline)	3,4-Diethoxy-5-methoxy-PEA	Scaline (mod.)	200–280 mg	10–15 hours	[9]
10	B (buscaline)	4-Butoxy-3,5-dimethoxy-PEA	Scaline	>150 mg	"Several hours"	[10]
11	BEATRICE (N-methyl-DOM)	2,5-Dimethoxy-4,N-dimethyl-A	DOx	>30 mg	6–10 hours	[11]
12	Bis-TOM	2,5-Bismethylthio-4-methyl-A	DOx (mod.)	>160 mg	Unknown	[12]
13	BOB (β-methoxy-2C-B)	4-Bromo-2,5,β-trimethoxy-PEA	BOx, 2C	10–20 mg	10–20 hours	[13]
14	BOD (β-methoxy-2C-D)	2,5,β-Trimethoxy-4-methyl-PEA	BOx, 2C	15–25 mg	8–16 hours	[14]
15	BOH (β-methoxy-MDPEA)	β-Methoxy-3,4-methylenedioxy-PEA	BOx, MDxx	80–120 mg	6–8 hours	[15]
16	BOHD (β-hydroxy-2C-D)	2,5-Dimethoxy-β-hydroxy-4-methyl-PEA	BOx, 2C	>50 mg	Unknown	[16]
17	BOM (β-methoxymescaline)	3,4,5,β-Tetramethoxy-PEA	BOx, scaline	>200 mg	Unknown	[17]
18	4-Br-3,5-DMA	4-Bromo-3,5-dimethoxy-A	3C-scaline	4–10 mg	8–12 hours	[18]
19	2-Br-4,5-MDA	2-Bromo-4,5-methylenedioxy-A	MDxx	350 mg	Unknown	[19]
20	2C-B	4-Bromo-2,5-dimethoxy-PEA	2C	12–24 mg	4–8 hours	[20]
21	3C-BZ (3C-benzscaline)	4-Benzyloxy-3,5-dimethoxy-A	3C-scaline	25–200 mg	18–24 hours	[21]
22	2C-C	4-Chloro-2,5-dimethoxy-PEA	2C	20–40 mg	4–8 hours	[22]
23	2C-D	4-Methyl-2,5-dimethoxy-PEA	2C	20–60 mg	4–6 hours	[23]
24	2C-E	4-Ethyl-2,5-dimethoxy-PEA	2C	10–25 mg	8–12 hours	[24]
25	3C-E (3C-escaline)	4-Ethoxy-3,5-dimethoxy-A	3C-scaline	30–60 mg	8–12 hours	[25]
26	2C-F	4-Fluoro-2,5-dimethoxy-PEA	2C	>250 mg	Unknown	[26]
27	2C-G	3,4-Dimethyl-2,5-dimethoxy-PEA	2C	20–35 mg	18–30 hours	[27]
28	2C-G-3	3,4-Trimethylene-2,5-dimethoxy-PEA	2C (mod.)	16–25 mg	12–24 hours	[28]
29	2C-G-4	3,4-Tetramethylene-2,5-dimethoxy-PEA	2C (mod.)	Unknown	Unknown	[29]
30	2C-G-5	3,4-Norbornyl-2,5-dimethoxy-PEA	2C (mod.)	10–16 mg	32–48 hours	[30]
31	2C-G-N	1,4-Dimethoxynaphthyl-2-ethylamine	2C (mod.)	20–40 mg	20–30 hours	[31]
32	2C-H (2,5-DMPEA)	2,5-Dimethoxy-PEA	2C	Unknown	Unknown	[32]
33	2C-I	4-Iodo-2,5-dimethoxy-PEA	2C	14–22 mg	6–10 hours	[33]
34	2C-N	4-Nitro-2,5-dimethoxy-PEA	2C	100–150 mg	4–6 hours	[34]
35	2C-O-4	4-Isopropoxy-2,5-dimethoxy-PEA	2C	>60 mg	Unknown	[35]
36	2C-P	4-Propyl-2,5-dimethoxy-PEA	2C	6–10 mg	10–16 hours	[36]
37	CPM (cyclopropylmescaline)	4-Cyclopropylmethoxy-3,5-dimethoxy-PEA	Scaline	60–80 mg	12–18 hours	[37]
38	2C-Se	4-Methylseleno-2,5-dimethoxy-PEA	2C	~100 mg	6–8 hours	[38]
39	2C-T	4-Methylthio-2,5-dimethoxy-PEA	2C	60–100 mg	3–5 hours	[39]
40	2C-T-2	4-Ethylthio-2,5-dimethoxy-PEA	2C	12–25 mg	6–8 hours	[40]
41	2C-T-4	4-Isopropylthio-2,5-dimethoxy-PEA	2C	8–20 mg	12–18 hours	[41]
42	Psi-2C-T-4 (ψ-2C-T-4)	4-Isopropylthio-2,6-dimethoxy-PEA	ψ-PEA	>12 mg	"Probably short"	[42]
43	2C-T-7	4-Propylthio-2,5-dimethoxy-PEA	2C	10–30 mg	8–15 hours	[43]
44	2C-T-8	4-Cyclopropylmethylthio-2,5-dimethoxy-PEA	2C	30–50 mg	10–15 hours	[44]
45	2C-T-9	4-(t)-Butylthio-2,5-dimethoxy-PEA	2C	60–100 mg	12–18 hours	[45]
46	2C-T-13	4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA	2C	25–40 mg	6–8 hours	[46]
47	2C-T-15	4-Cyclopropylthio-2,5-dimethoxy-PEA	2C	>30 mg	"Several hours"	[47]
48	2C-T-17	4-(s)-Butylthio-2,5-dimethoxy-PEA	2C	60–100 mg	10–15 hours	[48]
49	2C-T-21	4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA	2C	8–12 mg	7–10 hours	[49]
50	4-D (4-trideuteromescaline)	4-Trideuteromethyl-3,5-dimethoxy-PEA	Scaline	~200–400 mg^c	12 hours	[50]
51	Beta-D (β,β-dideuteromescaline)	β,β-Dideutero-3,4,5-trimethoxy-PEA	Scaline	~200–400 mg^c	12 hours	[51]
52	DESOXY (4-desoxymescaline)	4-Methyl-3,5-dimethoxy-PEA	Scaline (mod.)	40–120 mg	6–8 hours	[52]
53	2,4-DMA	2,4-Dimethoxy-A	Other	>60 mg	"Short"	[53]
54	2,5-DMA (DOH)	2,5-Dimethoxy-A	DOx	80–160 mg	6–8 hours	[54]
55	3,4-DMA (DMA)	3,4-Dimethoxy-A	Other	"A few [100 mg]"	Unknown	[55]
56	DMCPA	2,5-Dimethoxy-4-methyl-PCPA	DOx (mod.)	15–20 mg	4–8 hours	[56]
57	DME (β-hydroxy-3,4-DMPEA)	3,4-Dimethoxy-β-hydroxy-PEA	BOx, other	>115 mg	Unknown	[57]
58	DMMDA (2,5-dimethoxy-MDA)	2,5-Dimethoxy-3,4-methylenedioxy-A	MDxx	30–75 mg	6–8 hours	[58]
59	DMMDA-2 (5,6-dimethoxy-MDA)	2,3-Dimethoxy-4,5-methylenedioxy-A	MDxx	~50 mg	Unknown	[59]
60	DMPEA (3,4-DMPEA)	3,4-Dimethoxy-PEA	Other	>1,000 mg	Unknown	[60]
61	DOAM	4-Amyl-2,5-dimethoxy-A	DOx	>10 mg	Unknown	[61]
62	DOB	4-Bromo-2,5-dimethoxy-A	DOx	1–3 mg	18–30 hours	[62]
63	DOBU	4-Butyl-2,5-dimethoxy-A	DOx	Uncertain	"Very long"	[63]
64	DOC	4-Chloro-2,5-dimethoxy-A	DOx	1.5–3 mg	12–24 hours	[64]
65	DOEF	4-(2-Fluoroethyl)-2,5-dimethoxy-A	DOx	2–3.5 mg	12–16 hours	[65]
66	DOET	4-Ethyl-2,5-dimethoxy-A	DOx	2–6 mg	14–20 hours	[66]
67	DOI	4-Iodo-2,5-dimethoxy-A	DOx	1.5–3 mg	16–30 hours	[67]
68	DOM (STP)	4-Methyl-2,5-dimethoxy-A	DOx	3–10 mg	14–20 hours	[68]
69	Psi-DOM (ψ-DOM)	4-Methyl-2,6-dimethoxy-A	ψ-PEA	15–25 mg	6–8 hours	[69]
70	DON	4-Nitro-2,5-dimethoxy-A	DOx	3–4.5 mg	8–15 hours	[70]
71	DOPR	4-Propyl-2,5-dimethoxy-A	DOx	2.5–5 mg	20–30 hours	[71]
72	E (escaline)	4-Ethoxy-3,5-dimethoxy-PEA	Scaline	40–60 mg	8–12 hours	[72]
73	EEE	2,4,5-Triethoxy-A	DOx (mod.)	Unknown	Unknown	[73]
74	EEM	2,4-Diethoxy-5-methoxy-A	DOx (mod.)	Unknown	Unknown	[74]
75	EME	2,5-Diethoxy-4-methoxy-A	DOx (mod.)	Unknown	Unknown	[75]
76	EMM	2-Ethoxy-4,5-dimethoxy-A	DOx (mod.)	>50 mg	Unknown	[76]
77	ETHYL-J (EBDB)	N,α-Diethyl-3,4-methylenedioxy-PEA	MDxx	>90 mg	"Probably short"	[77]
78	ETHYL-K (EBDP)	N-Ethyl-α-propyl-3,4-methylenedioxy-PEA	MDxx	>40 mg	Unknown	[78]
79	F-2	2-Methyl-5-methoxy-2,3-dihydro-6-APBF	Benzofuran	>15 mg	Unknown	[79]
80	F-22	2,2-Dimethyl-5-methoxy-2,3-dihydro-6-APBF	Benzofuran	>15 mg	Unknown	[80]
81	FLEA (MDMOH)	N-Hydroxy-N-methyl-3,4-methylenedioxy-A	MDxx	100–160 mg	4–8 hours	[81]
82	G-3	3,4-Trimethylene-2,5-dimethoxy-A	DOx (mod.)	12–18 mg	8–12 hours	[82]
83	G-4	3,4-Tetramethylene-2,5-dimethoxy-A	DOx (mod.)	Unknown	Unknown	[83]
84	G-5	3,4-Norbornyl-2,5-dimethoxy-A	DOx (mod.)	14–20 mg	16–30 hours	[84]
85	GANESHA (G; 3-methyl-DOM)	3,4-Dimethyl-2,5-dimethoxy-A	DOx	20–32 mg	18–24 hours	[85]
86	G-N	1,4-Dimethoxynaphthyl-2-isopropylamine	DOx (mod.)	Unknown	Unknown	[86]
87	HOT-2 (N-hydroxy-2C-T-2)	2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA	HOT-x, 2C	10–18 mg	6–10 hours	[87]
88	HOT-7 (N-hydroxy-2C-T-7)	2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA	HOT-x, 2C	15–25 mg	6–8 hours	[88]
89	HOT-17 (N-hydroxy-2C-T-17)	2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA	HOT-x, 2C	70–120 mg	12–18 hours	[89]
90	IDNNA (N,N-dimethyl-DOI)	2,5-Dimethoxy-N,N-dimethyl-4-iodo-A	DOx	>2.6 mg	Unknown	[90]
91	IM (isomescaline)	2,3,4-Trimethoxy-PEA	Scaline (mod.)	>400 mg	Unknown	[91]
92	IP (isoproscaline)	3,5-Dimethoxy-4-isopropoxy-PEA	Scaline (mod.)	40–80 mg	10–16 hours	[92]
93	IRIS	5-Ethoxy-2-methoxy-4-methyl-A	DOx (mod.)	>9 mg	Unknown	[93]
94	J (BDB)	α-Ethyl-3,4-methylenedioxy-PEA	MDxx	150–230 mg	4–8 hours	[94]
95	LOPHOPHINE (MMDPEA)	3-Methoxy-4,5-methylenedioxy-PEA	MDxx	>200 mg	Unknown	[95]
96	M (mescaline; 3,4,5-TMPEA)	3,4,5-Trimethoxy-PEA	Scaline	~200–400 mg^c	10–12 hours	[96]
97	4-MA (PMA)	4-Methoxy-A	Other	50–80 mg	"Short"	[97]
98	MADAM-6 (6-methyl-MDMA)	2,N-Dimethyl-4,5-methylenedioxy-A	MDxx	>280 mg	Unknown	[98]
99	MAL (methallylescaline)	3,5-Dimethoxy-4-methallyloxy-PEA	Scaline	40–65 mg	12–16 hours	[99]
100	MDA	3,4-Methylenedioxy-A	MDxx	80–160 mg	4–6 hours^d	[100]
101	MDAL	N-Allyl-3,4-methylenedioxy-A	MDxx	>180 mg	Unknown	[101]
102	MDBU	N-Butyl-3,4-methylenedioxy-A	MDxx	>40 mg	Unknown	[102]
103	MDBZ	N-Benzyl-3,4-methylenedioxy-A	MDxx	>150 mg	Unknown	[103]
104	MDCPM	N-Cyclopropylmethyl-3,4-methylenedioxy-A	MDxx	>10 mg	Unknown	[104]
105	MDDM	N,N-Dimethyl-3,4-methylenedioxy-A	MDxx	>150 mg	Unknown	[105]
106	MDE (MDEA)	N-Ethyl-3,4-methylenedioxy-A	MDxx	100–200 mg	3–5 hours	[106]
107	MDHOET	N-(2-Hydroxyethyl)-3,4-methylenedioxy-A	MDxx	>50 mg	Unknown	[107]
108	MDIP	N-Isopropyl-3,4-methylenedioxy-A	MDxx	>250 mg	Unknown	[108]
109	MDMA	N-Methyl-3,4-methylenedioxy-A	MDxx	80–150 mg	4–6 hours	[109]
110	MDMC (EDMA)	N-Methyl-3,4-ethylenedioxy-A	EDxx	≥200 mg	3–5 hours	[110]
111	MDMEO	N-Methoxy-3,4-methylenedioxy-A	MDxx	>180 mg	Unknown	[111]
112	MDMEOET	N-(2-Methoxyethyl)-3,4-methylenedioxy-A	MDxx	>180 mg	Unknown	[112]
113	MDMP	α,α,N-Trimethyl-3,4-methylenedioxy-PEA	MDxx	~110 mg	~6 hours	[113]
114	MDOH	N-Hydroxy-3,4-methylenedioxy-A	MDxx	100–160 mg	3–6 hours	[114]
115	MDPEA	3,4-Methylenedioxy-PEA	MDxx	>300 mg	Unknown	[115]
116	MDPH	α,α-Dimethyl-3,4-methylenedioxy-PEA	MDxx	160–240 mg	3–5 hours	[116]
117	MDPL	N-Propargyl-3,4-methylenedioxy-A	MDxx	>150 mg	Unknown	[117]
118	MDPR	N-Propyl-3,4-methylenedioxy-A	MDxx	>200 mg	Unknown	[118]
119	ME (metaescaline)	3,4-Dimethoxy-5-ethoxy-PEA	Scaline (mod.)	200–350 mg	8–12 hours	[119]
120	MEDA (5-methoxy-EDA)	3-Methoxy-4,5-ethylenedioxy-A	EDxx	>200 mg	Unknown	[120]
121	MEE	2-Methoxy-4,5-diethoxy-A	DOx (mod.)	>4.6 mg	Unknown	[121]
122	MEM	2,5-Dimethoxy-4-ethoxy-A	DOx	20–50 mg	10–14 hours	[122]
123	MEPEA	3-Methoxy-4-ethoxy-PEA	Other	≥300 mg	"Short"	[123]
124	Meta-DOB	5-Bromo-2,4-dimethoxy-A	DOx (mod.)	50–100 mg	5–6 hours	[124]
125	Meta-DOT	5-Methylthio-2,4-dimethoxy-A	DOx (mod.)	>35 mg	Unknown	[125]
126	Methyl-DMA (N-methyl-2,5-DMA)	N-Methyl-2,5-dimethoxy-A	DOx	>250 mg	Unknown	[126]
127	Methyl-DOB (N-methyl-DOB)	4-Bromo-2,5-dimethoxy-N-methyl-A	DOx	>8 mg	"Probably long"	[127]
128	Methyl-J (MBDB)	N-Methyl-α-ethyl-3,4-methylenedioxy-PEA	MDxx	180–210 mg	4–6 hours	[128]
129	Methyl-K (MBDP)	N-Methyl-α-propyl-3,4-methylenedioxy-PEA	MDxx	>100 mg	Unknown	[129]
130	Methyl-MA (PMMA)	N-Methyl-4-methoxy-A	Other	>100 mg	"Short"	[130]
131	Methyl-MMDA-2 (6-methoxy-MDMA)	N-Methyl-2-methoxy-4,5-methylenedioxy-A	MDxx	>70 mg	Unknown	[131]
132	MMDA (5-methoxy-MDA)	3-Methoxy-4,5-methylenedioxy-A	MDxx	100–250 mg	"Moderate"	[132]
133	MMDA-2 (6-methoxy-MDA)	2-Methoxy-4,5-methylenedioxy-A	MDxx	25–50 mg	8–12 hours	[133]
134	MMDA-3a (2-methoxy-MDA)	2-Methoxy-3,4-methylenedioxy-A	MDxx	20–80 mg	10–16 hours	[134]
135	MMDA-3b (4-methoxy-2,3-MDA)	4-Methoxy-2,3-methylenedioxy-A	MDxx	>80 mg	Unknown	[135]
136	MME	2,4-Dimethoxy-5-ethoxy-A	DOx (mod.)	≥40 mg	~6–10 hours	[136]
137	MP (metaproscaline)	3,4-Dimethoxy-5-propoxy-PEA	Scaline (mod.)	>240 mg	Unknown	[137]
138	MPM	2,5-Dimethoxy-4-propoxy-A	DOx	≥30 mg	"Probably short"	[138]
139	Ortho-DOT	2-Methylthio-4,5-dimethoxy-A	DOx (mod.)	>25 mg	Unknown	[139]
140	P (proscaline)	3,5-Dimethoxy-4-propoxy-PEA	Scaline	30–60 mg	8–12 hours	[140]
141	PE (phenescaline)	3,5-Dimethoxy-4-phenethyloxy-PEA	Scaline	>150 mg	Unknown	[141]
142	PEA (phenethylamine)	PEA	Other	>1,600 mg	Unknown	[142]
143	PROPYNYL (propynylscaline)	4-Propynyloxy-3,5-dimethoxy-PEA	Scaline	≥80 mg	8–12 hours	[143]
144	SB (symbescaline)	3,5-Diethoxy-4-methoxy-PEA	Scaline (mod.)	>240 mg	Unknown	[144]
145	TA (TeMA)	2,3,4,5-Tetramethoxy-A	Other	>~50 mg	Unknown	[145]
146	3-TASB (3-thioasymbescaline)	4-Ethoxy-3-ethylthio-5-methoxy-PEA	Scaline (mod.)	~160 mg	10–18 hours	[146]
147	4-TASB (4-thioasymbescaline)	3-Ethoxy-4-ethylthio-5-methoxy-PEA	Scaline (mod.)	60–100 mg	10–15 hours	[147]
148	5-TASB (5-thioasymbescaline)	3,4-Diethoxy-5-methylthio-PEA	Scaline (mod.)	~160 mg	~8 hours	[148]
149	TB (thiobuscaline)	4-Thiobutoxy-3,5-dimethoxy-PEA	Scaline (mod.)	60–120 mg	~8 hours	[149]
150	3-TE (3-thioescaline)	4-Ethoxy-5-methoxy-3-methylthio-PEA	Scaline (mod.)	60–80 mg	8–12 hours	[150]
151	4-TE (4-thioescaline)	3,5-Dimethoxy-4-ethylthio-PEA	Scaline (mod.)	20–30 mg	9–12 hours	[151]
152	2-TIM (2-thioisomescaline)	2-Methylthio-3,4-dimethoxy-PEA	Scaline (mod.)	>240 mg	Unknown	[152]
153	3-TIM (3-thioisomescaline)	3-Methylthio-2,4-dimethoxy-PEA	Scaline (mod.)	>240 mg	Unknown	[153]
154	4-TIM (4-thioisomescaline)	4-Methylthio-2,3-dimethoxy-PEA	Scaline (mod.)	>160 mg	Unknown	[154]
155	3-TM (3-thiomescaline)	3-Methylthio-4,5-dimethoxy-PEA	Scaline (mod.)	60–100 mg	8–12 hours	[155]
156	4-TM (4-thiomescaline)	4-Methylthio-3,5-dimethoxy-PEA	Scaline (mod.)	20–40 mg	10–15 hours	[156]
157	TMA (α-methylmescaline)	3,4,5-Trimethoxy-A	3C-scaline	100–250 mg	6–8 hours	[157]
158	TMA-2 (DOMeO)	2,4,5-Trimethoxy-A	DOx	20–40 mg	8–12 hours	[158]
159	TMA-3	2,3,4-Trimethoxy-A	Other	>100 mg	Unknown	[159]
160	TMA-4	2,3,5-Trimethoxy-A	Other	>80 mg	~6 hours	[160]
161	TMA-5	2,3,6-Trimethoxy-A	Other	≥30 mg	8–10 hours	[161]
162	TMA-6 (ψ-TMA-2)	2,4,6-Trimethoxy-A	ψ-PEA	25–50 mg	12–16 hours	[162]
163	3-TME (3-thiometaescaline)	4,5-Dimethoxy-3-ethylthio-PEA	Scaline (mod.)	60–100 mg	10–15 hours	[163]
164	4-TME (4-thiometaescaline)	3-Ethoxy-5-methoxy-4-methylthio-PEA	Scaline (mod.)	60–100 mg	10–15 hours	[164]
165	5-TME (5-thiometaescaline)	3-Ethoxy-4-methoxy-5-methylthio-PEA	Scaline (mod.)	>200 mg	Unknown	[165]
166	2T-MMDA-3a (2-methylthio-MDA)	2-Methylthio-3,4-methylenedioxy-A	MDxx	>12 mg	Unknown	[166]
167	4T-MMDA-2 (4-thio-MMDA-2)	4,5-Thiomethyleneoxy-2-methoxy-A	MDxx (mod.)	>25 mg	Unknown	[167]
168	TMPEA (2,4,5-TMPEA; 2C-O)	2,4,5-Trimethoxy-PEA	2C	>300 mg	Unknown	[168]
169	2-TOET	4-Ethyl-5-methoxy-2-methylthio-A	DOx (mod.)	>65 mg	Unknown	[169]
170	5-TOET	4-Ethyl-2-methoxy-5-methylthio-A	DOx (mod.)	12–25 mg	8–24 hours	[170]
171	2-TOM	5-Methoxy-4-methyl-2-methylthio-A	DOx (mod.)	60–100 mg	8–10 hours	[171]
172	5-TOM	2-Methoxy-4-methyl-5-methylthio-A	DOx (mod.)	30–50 mg	6–10 hours	[172]
173	TOMSO	2-Methoxy-4-methyl-5-methylsulfinyl-A	DOx (mod.)	≥100–150 mg^e	10–16 hours	[173]
174	TP (thioproscaline)	4-Propylthio-3,5-dimethoxy-PEA	Scaline (mod.)	20–25 mg	10–15 hours	[174]
175	TRIS (trisescaline)	3,4,5-Triethoxy-PEA	Scaline (mod.)	>240 mg	Unknown	[175]
176	3-TSB (3-thiosymbescaline)	3-Ethoxy-5-ethylthio-4-methoxy-PEA	Scaline (mod.)	>200 mg	Unknown	[176]
177	4-TSB (4-thiosymbescaline)	3,5-Diethoxy-4-methylthio-PEA	Scaline (mod.)	>240 mg	Unknown	[177]
178	3-T-TRIS (3-thiotrisescaline)	4,5-Diethoxy-3-ethylthio-PEA	Scaline (mod.)	>160 mg	Unknown	[178]
179	4-T-TRIS (4-thiotrisescaline)	3,5-Diethoxy-4-ethylthio-PEA	Scaline (mod.)	>200 mg	Unknown	[179]
Acronyms (in chemical names): PEA =phenethylamine; A =amphetamine; PCPA =2-phenylcyclopropylamine; 6-APBF =6-(2-aminopropyl)benzofuran.Footnotes:^a =Dose andduration for compounds areorally unless otherwise specified.^b =Ariadne dose is as apsychedelic. Otherwise doses of 12–32 mg as theracemate and 25 mg as (R)-Ariadne were active.^c =4-D,beta-D, andmescaline doses are 200–400 mg as thesulfate salt and 178–356 mg as thehydrochloride salt.^d =MDA duration was originally 8–12 hours but was later revised by Shulgin to 4–6 hours in September 2001 following the publication ofPiHKAL.^e =TOMSO dose is >150 mg alone or 100–150 mg withalcohol.

In addition toPiHKAL, Shulgin has also described the properties of psychedelic phenethylamines in humans inliterature reviews.^[13]^[14]^[15]^[16]^[17]^[18]

References

[edit]

^Johnson, C. (2018).Magic Medicine: A Trip Through the Intoxicating History and Modern-Day Use of Psychedelic Plants and Substances. Fair Winds Press. pp. 22–24.ISBN 978-1-63159-428-1. RetrievedJanuary 30, 2025.
^^a ^b ^c ^dWalker, Scott R.; Pullella, Glenn A.; Piggott, Matthew J.; Duggan, Peter J. (July 17, 2023)."Introduction to the chemistry and pharmacology of psychedelic drugs".Australian Journal of Chemistry.76 (5):236–257.doi:10.1071/CH23050.ISSN 0004-9425. RetrievedNovember 1, 2025.Prior to its use being criminalised, mescaline (4) also played a significant role in the development of the synthetic phenethylamines by inspiring the investigations of medicinal chemist Alexander Shulgin. Shulgin synthesised at least 179 phenethylamines, which he then tested either alone on himself or along with his wife and close friends, referred to as the 'research group'.[85 ] This work established some structure–psychoactivity relationships for phenethylamines in humans and resulted in the discovery of a number of substituted phenethylamines that remain important, such as the 'classic hallucinogens' DOM (2,5-dimethoxy-4-methylamphetamine; 40) and 2C-B (2,5-dimethoxy-4-bromophenethylamine; 44, Fig. 10), and entactogens MDEA (3,4-methylenedioxy-N-ethylamphetamine; 38) and MBDB (N-methyl-1-(benzodioxol-5-yl)butan-2-amine; 36, Fig. 9). Alexander (Sasha) and Ann Shulgin's book Phenethylamines I have known and loved (PiHKAL)[85] is a seminal work that contains frank and detailed descriptions of the subjective effects of phenethylamines and remains extremely valuable to current phenethylamine research.
^^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^oAlexander T. Shulgin;Ann Shulgin (1991).PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA:Transform Press.ISBN 978-0-9630096-0-9.OCLC 25627628.
^Ben Sessa (2015). "Continuing History of Psychedelics in Medical Practices: The Renaissance of Ps chedelic Medical Research". In Ellens, J.H.; D, T.B.R.P. (eds.).The Psychedelic Policy Quagmire: Health, Law, Freedom, and Society. Psychology, Religion, and Spirituality. Bloomsbury Publishing. p. 50.ISBN 979-8-216-13356-8. RetrievedJanuary 30, 2025.
^Alexander T. Shulgin;Ann Shulgin (1997).TiHKAL: The Continuation (1st ed.). Berkeley, CA:Transform Press.ISBN 978-0-9630096-9-2.OCLC 38503252. RetrievedJanuary 30, 2025.
^Connie Littlefield (director, writer), Siobhan Flanagan,Alexander Shulgin (subject),Ann Shulgin (subject), Paul F. Daley (subject),Myron Stolaroff (subject), Jean Stolaroff (subject), Wendy Perry Tucker (subject), Tania Manning (subject), Greg Manning (subject),Keeper Trout (subject),Earth and Fire Erowid, others (2021).Better Living Through Chemistry (Motion picture). Better Living Through Film, Incorporated. Archived fromthe original on September 21, 2021.
^Passie T, Brandt SD (2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective".Handb Exp Pharmacol.252:69–110.doi:10.1007/164_2018_177.PMID 30478735.More ambitious explorations of subjective effects elicited by a series of new psychoactive substances developed by Shulgin were conducted by his close associate and psychologist, Myron Stolaroff. Following SEs with LSD in the mid-1950s, Stolaroff became involved in scientific research on psychedelics. After the control of most psychedelic drugs in the 1970s, Stolaroff conducted SEs with newly synthesized psychedelics 2C-B, 2C-E, 2C-T-2, 2C-T-7, 2C-T4, 2C-T-21, and MEM but also MDMA. Besides Shulgin, Stolaroff was the first who systematically explored the psychological states and their possible uses but under noncontrolled conditions (Stolaroff 1994). He understood his research as an attempt "to make the unconscious conscious" and to give some "guidelines for the proper and safe use of psychedelic drugs in therapy and for spiritual growth" (Stolaroff 1994, pp. 13–14).
^Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013)."2C or not 2C: phenethylamine designer drug review".J Med Toxicol.9 (2):172–178.doi:10.1007/s13181-013-0295-x.PMC 3657019.PMID 23494844.
^Bennett, Drake (January 30, 2005)."Dr. Ecstasy".New York Times Magazine.
^"Controlled Substances"(PDF).Drug Enforcement Administration. February 2016. Archived fromthe original(PDF) on April 17, 2016. RetrievedApril 13, 2016.
^^a ^b ^cGer A, Ger D."Triple Goddess of the Night".British Neuroscience Association Bulletin.63:28–30.
^Trachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag.ISBN 978-3-03788-700-4.OCLC 858805226. Archived fromthe original on August 21, 2025.
^Jacob P, Shulgin AT (1994)."Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.).Hallucinogens: An Update(PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91.PMID 8742795. Archived fromthe original on July 13, 2025.
^Shulgin AT (2003)."Basic Pharmacology and Effects". In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137.ISBN 978-0-12-433951-4. Archived fromthe original on July 13, 2025.
^Shulgin AT (1978)."Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.).Stimulants. Boston, MA: Springer US. pp. 243–333.doi:10.1007/978-1-4757-0510-2_6.ISBN 978-1-4757-0512-6.
^Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978)."Mescaline analogs: substitutions at the 4-position"(PDF).NIDA Res Monogr (22):27–37.PMID 101882. Archived fromthe original(PDF) on August 5, 2023.
^Shulgin AT (1980)."Hallucinogens". In Burger A, Wolf ME (eds.).Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137.ISBN 978-0-471-01572-7.OCLC 219960627.
^Shulgin AT (1982)."Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.).Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29.doi:10.1007/978-3-642-67770-0_1.ISBN 978-3-642-67772-4.OCLC 8130916.

External links

[edit]

Phenethylamines

Entactogens:Lophophine
MDPEA
MDMPEA

Amphetamines

Phentermines

Entactogens:MDPH
MDMPH

Others:Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants:α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine TehaunineN-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232
Others / unsorted	1-Aminomethylindanes (e.g.,2CB-Ind,AMMI,bromojimscaline,jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam,lorcaserin,7-chlorolorcaserin,SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48,Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g.,adrenochrome,adrenolutin) Benzocyclobutenes (e.g.,2CBCB-NBOMe,bromotomscaline,S33005,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) Butyltolylquinuclidine Camfetamine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI,RU-27849,DEIMDHPCA,DEMPDHPCA,DEMPDHPCA-2C-D,RU-27251) PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA,TMT,tranylcypromine) Phenylpiracetams (e.g.,phenylpiracetam,MRZ-9547,RGPU-95) Pyridopyrroloquinoxalines (e.g.,lumateperone,deulumateperone,IHCH-7079,IHCH-7086,IHCH-7113,ITI-1549) Tetrahydrobenzopyranylamines (e.g.,CT-5126) Tolazoline Tricyclics (e.g.,AMDA,AMDH,benzoctamine,dizocilpine,SpAMDA) ZC-B

Related compounds

2-Furylethylamine
2-Pyrrolylethylamine
3-Pyrrolylethylamine
3-Pyrrolylpropylamine
2-Tetrahydrofurylethylamine
4-Benzylpiperidine
7-AB
Alkylamines (e.g.,1,3-DMBATooltip 1,3-dimethylbutylamine,1,4-DMAATooltip 1,4-dimethylamylamine,heptaminol,iproheptine,isometheptene,methylhexanamine/1,3-DMAA,octodrine,oenethyl,tuaminoheptane)
Benzylamines (e.g.,benzylamine,α-methylbenzylamine,MDM1EA,ALPHA,M-ALPHA,pargyline)
Benzylpiperazines (e.g.,benzylpiperazine,MDBZP,fipexide)
Cyclohexylaminopropanes (e.g.,propylhexedrine,norpropylhexedrine)
Cyclopentylaminopropanes (e.g.,isocyclamine,cyclopentamine)
Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine,CT-4719,ORG-37684)
Phenylalkenylamines (e.g.,phenylbutenamine)
Phenylalkynylamines (e.g.,phenylbutynamine)
Phenylpiperazines (e.g.,1-phenylpiperazine,mCPPTooltip meta-chlorophenylpiperazine,TFMPPTooltip trifluoromethylphenylpiperazine,oMPPTooltip ortho-methylphenylpiperazine,pFPPTooltip para-fluorophenylpiperazine,pMeOPPTooltip para-methoxyphenylpiperazine)
Phenylpropylamines (e.g.,phenylpropylamine,homo-MDA,homo-MDMA)
Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine,methiopropamine,thiothinone)

Psychedelics

Tryptamines

No ring subs.	CYB004 (deuDMT) DALT DBT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT MET MiPT MPT NBoc-DMT NMT PALT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT 4-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines:Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acetoxytryptamines:4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MALT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT Luvesilocin (4-GO-DiPT; RE-104, FT-104)
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines:O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT ASR-3001 (5-MeO-iPALT)
Other ring subs.	2,N,N-TMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-N,N-TMT 7,N,N-TMT 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) α,N,N-TMT (α-Me-DMT; Alpha-N) N-Hydroxy-AMT 5-Methoxy-α-alkyltryptamines:5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g.,N-DEAOP-NET,N-DEAOP-NMT,5-MeO-N-DEAOP-NMT,5-MeO-N-DEAOP-NET) Structure undisclosed:CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g.,LSD) β-Carbolines andHarmala alkaloids (e.g.,harmine,harmaline,6-methoxyharmalan) Iboga alkaloids (e.g.,18-MAC,18-MC,coronaridine,ibogaine,ibogamine,ME-18-MC,noribogaine,tabernanthine,voacangine) Ibogalogs (e.g.,ibogainalog) O-Methylnordehydrobufotenine Partial ergolines (e.g.,NDTDI,RU-28306,CT-5252) Piperidinylethylindoles (e.g.,pip-T) Pyrrolidinylethylindoles (e.g.,pyr-T,5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g.,MPMI,4-HO-MPMI (lucigenol),5-MeO-MPMI) Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI),NEtPhOH-THPI)
Bioisosteres	Benzofurans (e.g.,5-MeO-DiBF,dimemebfe (5-MeO-BFE),mebfap) Benzothiophenes (e.g.,3-APBT) Indazolethylamines (e.g.,AL-38022A,O-methyl-AL-34662) Indenylethylamines (e.g.,C-DMT) Isotryptamines (e.g.,6-MeO-isoDMT,Ro60-0175) MYCO-005 Quinolinylethylamines (e.g.,mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline N,N-Diformylmescaline Escaline Fluoroescaline Fluoroproscaline N-Formylmescaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline Methallylescaline N-Methylmescaline (M-M) NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x:2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x:2C-O 2C-O-2 2C-O-4 Others:2C-B-AN 2C-DB 2C-G-x (e.g.,2C-G-3,2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g.,BOB,BOD,BOH-2C-B) HOT-x (e.g.,HOT-2,HOT-7,HOT-17) N-Ethyl-2C-B TWEETIOs (e.g.,2CD-2-ETO,2CD-5-ETO,2CE-5-ETO,2CE-5iPrO,2CT2-5-ETO,ASR-2001 (2CB-5PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA (3C-M)
DOx	DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x):Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx):MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others:DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g.,Ganesha (G, G-0) N-Hydroxy-DOM
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
Ψ-PEA	Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2)
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe:25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH:25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others:25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027
Others	2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM Benzofurans (e.g.,5-APB,5-APDB,6-APB,6-APDB,F,F-2,F-22) Benzothiophenes (e.g.,5-APBT,6-APBT) CT-5172 DMAs (e.g.,2,4-DMA,3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g.,25D-NM-NDEAOP,DOB-NDEPA,DOI-NDEPA,DOM-NDEPA,DOTFM-NDEPA,M-NDEPA,TMA-2-NDEPA) PMA (4-MA) TMAs (e.g.,TMA-3,TMA-4,TMA-5) TOMSO ZDCM-04 Structure undisclosed:CYB005
Cyclized	1-Aminomethylindanes (e.g.,2CB-Ind,jimscaline) 2-Aminoindanes (e.g.,DOM-AI) 3-Benzazepines (e.g.,lorcaserin) 3-Phenylpiperidines (e.g.,LPH-5,LPH-48) Benzocyclobutenes (e.g.,2CBCB-NBOMe,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g.,LSD) Glaucine Partial ergolines (e.g.,NDTDI,DEIMDHPCA,DEMPDHPCA,DEMTMPDHPCA,DEMNDHPCA) Phenylcyclopropylamines (e.g.,DMCPA,TMT) Phenyloxazolamines (aminorexes) (e.g.,2C-B-aminorex) Pyridopyrroloquinoxalines (e.g.,IHCH-7113) Z3517967757 ZC-B

Lysergamides

1-Alkyllysergamides (prodrugs):Methysergide (1-methylmethylergonovine; UML-491)
MLA-74 (1-methyl-LAE)
MLD-41 (1-methyl-LSD)
MPD-75 (1-methyl-LPD)
OML-632 (1-hydroxymethyl-LSD)

Other ring system-substituted lysergamides:12-Hydroxy-LSD
12-Methoxy-LSD

Bioisosteres:JRT

Others

Arylpiperazines (e.g.,2C-B-PP,2-NP,mCPP,MK-212,ORG-12962,pCPP,pFPP,quipazine,TFMPP)
Dihydrobenzoxazines (e.g.,efavirenz)
Phenoxyethylamines (e.g.,CT-4719,ORG-37684)
Pyridopyrroloquinoxalines (e.g.,IHCH-7113)
Quinazolinylethylamines (e.g.,RH-34)

Natural sources

Cyclized tryptamines:Banisteriopsis caapi (yagé)
Peganum harmala (Syrian rue)
Silene undulata
Tabernanthe iboga (iboga)

Phenethylamines:Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Echinopsis cacti (e.g.,San Pedro,Peruvian torch)

Entactogens

Phenethylamines

Non-ring-extended	Amphetamines:3-CMA 4-FA (PAL-303) 4-FMA 4-MA (PAL-313; Aptrol; normephedrine) 4-MMA (mephedrine) 4-MTA 4-MTMA (NMMTA; PAL-1063) MMA MMMA PMA PMEA PMMA Phenylisobutylamines:4-CAB (AEPCA) Cathinones:3-CMC (clophedrone; βk-3-CMA) 3-MMC (metaphedrone; βk-3-MMA) 4-EMC (βk-4-EMA) Brephedrone (4-BMC; βk-4-BMA) Flephedrone (4-FMC; βk-4-FMA) Mephedrone (4-MMC; 4-methylephedrone; βk-4-MMA) Methedrone (PMMC; βk-PMMA)
Benzodioxoles (methylenedioxy- or MDxx)	Phenethylamines:Lophophine (MMDPEA) Amphetamines:2-Methyl-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA EIDA Lys-MDA MDEA (MDE) MDMA (midomafetamine; ecstasy) (R)-MDMA (EMP-01; MM-402) MDMA/citalopram MDMOH (FLEA; MDHMA) MDOH (MDH) MMDA (5-methoxy-MDA) MMDMA (5-methoxy-MDMA) N-t-BOC-MDMA Phenylisobutylamines:BDB (J) EBDB (Ethyl-J) MBDB (Methyl-J) Phentermines:MDMP MDPH Cathinones:5-Methoxymethylone (2-A1MP; βk-MMDMA) 5-Methylethylone (5-methyl-βk-MDEA) Butylone (βk-MBDB) Dimethylone (βk-MDDMA) Ethylone (MDEC; βk-MDEA) Eutylone (βk-EBDB) Methylenedioxycathinone (MDC; βk-MDA) Methylone (MDMC; βk-MDMA) Putylone (βk-PBDB)
Benzodioxines (ethylenedioxy-)	Amphetamines:EDA EDMA Cathinones:EDMC
Benzofurans	Amphetamines:4-APB 5-APB 5-EAPB 5-MAPB 6-APB 6-EAPB 6-MAPB 7-APB Phenylisobutylamines:5-MBPB (5-MABB) 6-MBPB (6-MABB) Cathinones:BK-5-MAPB BK-6-MAPB
Dihydrobenzofurans	Amphetamines:5-APDB (EMA-4) 5-MAPDB 6-APDB (EMA-3) 6-MAPDB IBF5MAP (5-MAPP)
Benzothiophenes	Amphetamines:4-APBT 5-APBT 5-MAPBT(MY400) 6-APBT 6-MAPBT (MY300) 7-APBT Cathinones:BK-5-MAPBT
Benzothiazoles	Amphetamines:5-BZT-MDA 5-BZT-MDMA 6-BZT-MDA 6-BZT-MDMA
Benzoxathioles	Amphetamines:MY100 MY101 MY200
Indanes	Amphetamines:5-APDI (IAP) 5-MAPDI (IMP)
Indoles	Amphetamines:5-API (5-IT; PAL-571) 6-API (6-IT)
Naphthalenes	Amphetamines:Ethylnaphthylaminopropane (ENAP; PAL-1045) Methamnetamine (MNAP; PAL-1046; MY-10) Naphthylaminopropane (NAP; PAL-287)
Tetralins	Amphetamines:6-APT (TAP) Cathinones:TH-PVP
Others	Amphetamines:ODMA SeDMA TDMA Unknown:MYCO-002 MYCO-006 MYCO-007

Cyclized
phenethylamines

2-Aminoindanes	5-IAI BFAI ETAI MDAI MDMAI MEAI (5-MeO-AI; CMND-100) MMAI TAI
1-Aminomethylindanes	AMMI
2-Aminotetralins	6-CAT MDAT MDMAT
Aminorexes	4,4'-DMAR MDMAR

Tryptamines

α-Alkyltryptamines	4-Methyl-αET 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212, PAL-544) αET (etryptamine; Monase; PAL-125) αMT (Indopan; PAL-17; 3-API; 3-IT) β-Ketotryptamines:BK-NM-AMT BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT

Others

Benzofurans	2-APB 2-MAPB 3-APB
Benzothiophenes	2-APBT 3-APBT (SKF-6678)
Indolizines	1Z2MAP1O
Isotryptamines	isoAMT (PAL-569; 1-API; 1-IT)
Others	Borax combo (Blue Bliss, Pink Star) MDM1EA (α,N-DMMDBA) UnknownTACT411 TACT833 Atypical:2C-B 5-MeO-DiPT 5-MeO-MiPT

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine,Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa,Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine,Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine,Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Phenethylpyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Psychedelics	2,5-DMA (DOH) 2C-B 2C-D 2C-G-N 5-MeO-DiPT 5-MeO-MiPT Ariadne (4C-DOM; BL-3912; Dimoxamine) ASR-2001 (2CB-5PrO) DOET DOM DOPR LSD MTFEM
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code:N06B

v t e Chemical classes ofpsychoactive drugs
Stimulants	Amphetamine-type/dopamine releasing agents:Alkylamines Cycloalkylaminopropanes Arylpiperazines Benzylpiperazines Phenylpiperazines Phenethylamines Aminorexes/phenyloxazolamines Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines Phenylisobutylamines/α-ethylphenethylamines α-Propylphenethylamines Phenylmorpholines/phenmetrazines Thiopropamines/thienylaminopropanes Cocaine-type/typical dopamine reuptake inhibitors:Phenethylamines Phenidates/benzylpiperidines Phenylethylpyrrolidines Pyrrolidinophenones Phenyltropanes/cocaine analogues Modafinil-type/atypical dopamine reuptake inhibitors:Modafinil analogues Phenylpiracetams Caffeine-type/adenosine receptor antagonists:Xanthines/methylxanthines Nicotine-type/nicotinic acetylcholine receptor agonists:Nicotine analogues
Depressants	GABA_A receptor positive allosteric modulators:Alcohols/ethanol analogues Barbiturates Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Carbamates Ethers Neuroactive steroids Nonbenzodiazepines β-Carbolines Cyclopyrrolones Imidazopyridines Pyrazolopyrimidines Phenols Piperidinediones Quinazolinones GABA_A receptor agonists:Isoxazoles GHB receptor agonists:1,4-Butanediols α₂δ subunit-containing voltage-gated calcium channel blockers:Gabapentinoids Opioids/μ-opioid receptor agonists:Benzimidazoles Nitazenes Fentanyl analogues/phenylpiperidines Mitragyna alkaloids Morphinans/phenanthrenes Opiates/opium alkaloids Utopioids Antihistamines/H₁ receptor antagonists:Benzimidazoles Diarylmethanes Ethylenediamines Tricyclics Dibenzocycloheptenes
Hallucinogens	Serotonergic psychedelics/serotonin 5-HT_2A receptor agonists:Arylpiperazines Phenylpiperazines Quinolinylpiperazines Cyclized phenethylamines 3-Benzazepines Cyclized tryptamines Azepinoindoles Ibogalogs Iboga alkaloids β-Carbolines Harmala alkaloids Ergolines Lysergamides Simplified/partial lysergamides Phenethylamines (methoxyphenethylamines) 2Cs 25-NB/NBOMes 2C-Os 2C-Ts HOT-x TWEETIOs Amphetamines/α-methylphenethylamines 3Cs Dimethoxyamphetamines/DMAs DOx Alephs Ethylenedioxyamphetamines/EDxx Methylenedioxyamphetamines/MDxx Trimethoxyamphetamines/TMAs BOx FLYs/benzofurans Phenylisobutylamines/α-ethylphenethylamines 4Cs Scalines Ψ-PEAs Tryptamines α-Alkyltryptamines α-Alkyl-β-ketotryptamines 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Miscellaneous Dissociatives/NMDA receptor antagonists:Adamantanes Arylcyclohexylamines Diarylethylamines Morphinans κ-Opioid receptor agonists:Benzomorphans Salvinorins GABA_A receptor agonists:Isoxazoles Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists:Diarylmethanes Tropanes Others:Cyclized tryptamines Azepinoindoles Iboga alkaloids (Phyto)cannabinoids
Entactogens	Serotonin releasing agents:Phenethylamines 2-Aminoindanes 2-Aminotetralins Amphetamines Benzofuranylaminopropanes Benzothiophenylaminopropanes Ethylenedioxyamphetamines/EDxx Indanylaminopropanes Indolylaminopropanes Methylenedioxyamphetamines/MDxx Tetralinylaminopropanes Tryptamines α-Alkyltryptamines Miscellaneous
Psychiatric drugs	Anxiolytics:Azapirones Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Antidepressants:Tricyclic antidepressants Dibenzazepines Dibenzocycloheptenes Dibenzothiepins Dibenzoxazepines Dibenzoxepins Tetracyclic antidepressants Antipsychotics/dopamine D₂ receptor antagonists or partial agonists:Benzamides Benzimidazoles Benzisothiazoles Benzisoxazoles Butyrophenones Diphenylbutylpiperidines Phenylpiperazines Tricyclics Dibenzazepines Dibenzodiazepines Dibenzothiazepines Dibenzothiepins Dibenzoxazepines Phenothiazines Thienobenzodiazepines Mood stabilizers/anticonvulsants:Gabapentinoids Tricyclics Dibenzazepines Valproates
Others	Nootropics:Racetams Phenylpiracetams Miscellaneous:3-Benzazepines Adamantanes Catecholamines Tetrahydroisoquinolines Yohimbans