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NDTDI

From Wikipedia, the free encyclopedia
Chemical compound
This article is about 9-nor-LSD. For other nor-LSD compounds, seeNor-LSD (disambiguation).
Pharmaceutical compound
NDTDI
Clinical data
Other namesN-(2-Diethylcarbamoylethyl)-N-methyl-4,α-methylenetryptamine;N-(3-Diethylamino-3-oxopropyl)-N-methyl-4,α-methylenetryptamine; 9-Nor-LSD; 9-Desmethine-LSD; 8,10-Seco-LSD
Drug classSerotonergic psychedelic;Hallucinogen;Simplified/partial LSD analogue
ATC code
  • None
Legal status
Legal status
  • Illegal in Latvia
Identifiers
  • N,N-diethyl-3-(methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino)propanamide
PubChemCID
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC19H27N3O
Molar mass313.445 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)CCN(C)C1Cc3cccc2ncc(C1)c23
  • InChI=1S/C19H27N3O/c1-4-22(5-2)18(23)9-10-21(3)16-11-14-7-6-8-17-19(14)15(12-16)13-20-17/h6-8,13,16,20H,4-5,9-12H2,1-3H3
  • Key:JECGWOMOCPQHDH-UHFFFAOYSA-N

NDTDI, also known as9-desmethine-LSD,9-nor-LSD, or8,10-seco-LSD, is apsychedelic drug related tolysergic acid diethylamide (LSD).[1][2][3][4] It is atricycliccyclized tryptamine andpartial lysergamide and is astructurallysimplifiedanalogue of LSD.[2] The drug is specifically the analogue of LSD in which thecarbonatom at position 9 of theergolinering system has been removed.[2] It has been reported to produce psychedelic effects similarly to LSD, but with much lowerpotency.[1] Thepharmacology of NDTDI has not been studied. NDTDI was encountered as a noveldesigner drug by 2016.[1][3][4]

Structures ofLSD (left), NDTDI (4-desmethine-LSD) (middle), andN-DEAOP-NMT (desvinyl-LSD) (right).

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Chemistry

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Analogues

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Analogues of NDTDI includeRU-27849,RU-28306,RU-28251,Bay R 1531 (LY-197206),LY-293284, andLY-178210. Otherpartial/simplified lysergamides includeDEIMDHPCA (4-nor-LSD),DEMPDHPCA (dides-B,C-LSD), and10,11-seco-LSD, among others. Deletion of the carbon at positions 9 and 10 of the ergoline ring system result in a fully non-rigid tryptamine derivative,N-DEAOP-NMT (9,10-dinor-LSD).[5][6]

History

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NDTDI has been sold as adesigner drug since 2016 and was first identified by aforensiclaboratory inSlovenia in 2017.[3] NDTDI was made illegal inLatvia in March 2017.[4][7]

Society and culture

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Legal status

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Canada

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NDTDI is not an explicitly nor implicitlycontrolled substance inCanada as of 2025.[8]

United States

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NDTDI is not an explicitlycontrolled substance in theUnited States.[9] However, it could be considered a controlled substance under theFederal Analogue Act if intended for human consumption.

See also

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References

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  1. ^abc"Latvian authorities apply temporary restriction on new psychoactive substance".Baltic News Network. 6 March 2017. Retrieved30 January 2026.
  2. ^abc"N,N-Diethyl-N3-methyl-N3-(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)-I(2)-alaninamide".PubChem. Retrieved20 March 2025.
  3. ^abcAnalytical Report NDTDI (C19H27N3O) 3-({2-azatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),3,8(12),9-tetraen-6-yl}(methyl)amino)-N,N-diethylpropanamide(PDF), European Project Response
  4. ^abcAutorizēties savā kontā (March 2017)."Par aizlieguma noteikšanu vielai NDTDI un tās saturošiem izstrādājumiem" [On the prohibition of the substance NDTDI and products containing it].LIKUMI.LV (in Latvian). Retrieved20 March 2025.
  5. ^Nichols DE (May 1973).Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis).University of Iowa. p. 23.OCLC 1194694085.Sklar, et al. (53) found the diethylacrylamide adduct 20 to be approximately 1/10 as active as LSD in mice, although Norris and Blicke (54) reported 21 to have little oxytocic activity. [...] 20 = R = C2H5. 21 = R = CH3 [...]
  6. ^Norris PE, Blicke FF (December 1952). "Potential ergot substitutes: esters and amides of beta-amino acids".J Am Pharm Assoc.41 (12):637–639.doi:10.1002/jps.3030411204.PMID 13022416.Six esters and amides of derivatives of β-alanine which are related to lysergic acid have been prepared and tested for oxytocic activity. None of these products possess a significant oxytocic activity. [...] The purpose of this investigation was to synthesize amides and also esters of compounds (II–V) which represent fragments of the lysergic acid molecule in the hope that some of these products might possess oxytocic activity. Various modified fragments of the lysergic acid molecule have been synthesized previously; it was claimed that some of the compounds are active oxytocics (1—7). [...] Pharmacologic data indicated that none of the esters or amides of compounds II—V which were prepared possess a significant oxytocic action when compared to the clinically used oxytocics. However, the diethylamide of N-methyl-N-[β′-(3-indolyl)-ethyl]-β-alanine (IIIc) appeared to have an oxytocic activity approximately ten times stronger than that of the diethylamide of N-methyl-N-(β′-phenethyl)-β-alanine (IIc).
  7. ^"Par aizlieguma noteikšanu vielai NDTDI un tās…".www.vestnesis.lv (in Latvian). 6 March 2017. Retrieved30 January 2026.
  8. ^"Controlled Drugs and Substances Act".Department of Justice Canada. 5 December 2025. Retrieved20 January 2026.
  9. ^Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)(PDF),United States: U.S.Department of Justice:Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

External links

[edit]
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
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Natural sources
Tryptamines
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N-Acetyltryptamines
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α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
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