2C-D, also known as4-methyl-2,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine and2C families.[1] It has an unusually wide and gradual dose range and at low doses produces claimedcognitive enhancer-like effects, mildstimulant effects, and mildperceptual effects, whereas at high doses, it produces robust psychedelic effects.[2][1][3][4] The drug is takenorally.[1]
In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 2C-D's dose range as 20 to 60mgorally and itsduration as 4 to 6hours.[1][2] He describes threshold effects as occurring at a dose of 6mg orally and fullintoxication occurring at doses of 10 to 15mg orally.[2] Higher doses of 75 to 200mg orally have also been described and were well-tolerated.[1][3] In addition, a widerrecreational dose range of 3 to 100mg or more has been described.[23] Theonset is said to be 20 to 30minutes and peak effects occur after 1.5 to 2hours.[2]Casey Hardison has described 2C-D as having a very gentledose–response curve with an unusually wide dose range.[4]
The effects of 2C-D have been described.[2][1][3] At low doses, it produces perceivedcognitive enhancement, mildstimulant-like effects,emotional integration,euphoria, and mildpsychedelic effects such asperceptual enhancement that are much lighter than those of conventional psychedelics.[2][1][3] At high doses, it produces robust psychedelic effects.[1] Shulgin referred to 2C-D as a "pharmacologicaltofu" because it didn't have especially pronounced effects on its own until very high doses were reached but could be combined with and extend or potentiate the effects of other psychedelics without coloring their experiences.[4][1]
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:[26][27][5][6][28][7][8][29]
2C-D was first described in thescientific literature by Beng T. Ho and colleagues at the Texas Research Institute of Mental Sciences in 1970.[10][11] They described itssynthesis andpharmacological effects in animals.[10][11] The properties and effects of 2C-D in humans, along with those of2C-B, were described byAlexander Shulgin and Michael Carter in 1975.[2] Shulgin had first tested 2C-D at sub-threshold doses in 1964 and 1965.[31] Subsequently, he tested it at higher doses in 1974 and 1975 and discovered itspsychoactive effects.[32]
Sveriges riksdags health ministryStatens folkhälsoinstitut classified 2C-D as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as "2,5-dimetoxi-4-metylfenetylamin (2C-D)", making it illegal to sell or possess.[38]
2C-D became aSchedule I Controlled Substance in the United States as of July 9, 2012, with the signing of Food and Drug Administration Safety and Innovation Act.[39] On a state level, bothOklahoma andPennsylvania list 2C-D under schedule I.
^abcMoya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, et al. (June 2007). "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors".The Journal of Pharmacology and Experimental Therapeutics.321 (3):1054–1061.doi:10.1124/jpet.106.117507.PMID17337633.
^abcBrimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
^abcdHo BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT (January 1970). "Amphetamine analogs. II. Methylated phenethylamines".Journal of Medicinal Chemistry.13 (1):134–135.doi:10.1021/jm00295a034.PMID5412084.
^abcShulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN0-9630096-9-9.OCLC38503252. "At a banquet associated with an international conference on the study of consciousness, held in Göttingen a few years ago, Alice and I had the pleasure of sitting at the table with Hanscarl Leuner and his wife. He thanked me for inventing 2C-D which he and his students had been exploring as an adjunct to psychotherapy. They had renamed it, initially DMM-PEA and then LE-25, and had apparently explored it at dosages that reached into the hundreds of milligrams. In PIHKAL, I had offered an effective range for this drug of from 20 to 60 milligrams. It would seem that in his later years, Dr. Leuner chose to move from the psycholytic camp over to the psychedelic camp."
^abPoulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020)."DARK Classics in Chemical Neuroscience: NBOMes".ACS Chemical Neuroscience.11 (23):3860–3869.doi:10.1021/acschemneuro.9b00528.PMC9191638.PMID31657895.During the late 1970s and early 1980s, 2,5- dimethoxy-4-methylphenethylamine (2C-D), another compound from this class, received considerable attention from psychiatrists as a psychotherapeutic adjunct, most notably Hanscarl Leuner, who worked with 2C-D extensively under the code name LE-25 and pioneered the concept of psychedelic therapy.21 [...] (21). Leuner H (1981) Halluzinogene: Psychische Grenzzustände in Forschung und Psychotherapie, Hogrefe AG, Bern, Germany
^abPassie T (2024)."A history of the European Medical Society for Psycholytic Therapy (EPT) 1964–1974".Drug Science, Policy and Law.10 20503245231221154.doi:10.1177/20503245231221154.ISSN2050-3245.Like Jan Bastiaans, the Dutch chair of psychiatry at Leiden University, Leuner retained his license to use hallucinogens until his retirement in 1985. Leuner continued to conduct research on psycholytic therapy. There were studies on ketamine (Bolle, 1985, 1988), on the short-acting phenethylamine DMM-PEA (2C-D) (Schlichting, 1989, 1991), on the anal experience theme in psycholysis (Adler, 1981), and on results of other patients undergoing psycholysis (Schulz-Wittner, 1989). In Czechoslovakia and in England, psycholytic treatments were still carried out at some centers until the mid-1970s.
^abPassie T (7 November 2022)."History of the Use of Hallucinogens in Psychiatric Treatment". In Grob CS, Grigsby J (eds.).Handbook of Medical Hallucinogens. Guilford Publications. pp. 95–118.ISBN978-1-4625-5189-7.Also in the early 1950s, German psychiatrist Hanscarl Leuner (1984) developed guided affective imagery, a daydream technique used in psychotherapy. Concluding that small doses of hallucinogens may intensify imagery and induce regression and catharsis, Leuner (1959) began to use lowdose LSD with his psychotherapy patients. [...] During the 1960s, due to a continuous process of refinement, psycholytic therapists arrived at what might be considered today as a fully developed method (cf. Abramson, 1967; Grof, 1980b; Leuner, 1981). [...] Psycholytic therapy underwent a number of modifications during its active years. Some European therapists experimented with [...] the mescaline derivative 2-CD (2,5-dimethoxy-4-methylphenethylamine; Schlichting, 1989). [...] Leuner, H. (1981). Halluzinogene. Bern, Germany: Huber. [...] Schlichting, M. (1989). Psychotrope Eigenschaften des Phenäthylamins DMM-PEA (2,5-dimethoxy-4-methyl-phenathylamin). Unpublished doctoral thesis, Göttingen University, Göttingen, Germany.
^abcTheobald DS, Maurer HH (November 2006). "Studies on the metabolism and toxicological detection of the designer drug 2,5-dimethoxy-4-methyl-beta- phenethylamine (2C-D) in rat urine using gas chromatographic/mass spectrometric techniques".Journal of Mass Spectrometry.41 (11):1509–1519.Bibcode:2006JMSp...41.1509T.doi:10.1002/jms.1128.PMID17103384.2,5-Dimethoxy-4-methyl-ˇ-phenethylamine (2C-D) was described by Alexander Shulgin as a hallucinogenic substance.2 Descriptions and experience reports on internet web sites (http//:www.erowid.org, http//:www.lycaeum.org; June 2006) indicate that 2C-D plays a role among drug abusers. Furthermore, 2C-D was identified on the illicit drug market in the US.3–5 In most countries, 2C-D is not a controlled substance. This fact may enhance its popularity among drug abusers because the more popular members of the 2C-series like 2C-B or 2C-T-7 are scheduled now in many countries.
^abTheobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)".Biochemical Pharmacology.73 (2):287–297.doi:10.1016/j.bcp.2006.09.022.PMID17067556.
^Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor".Archives of Toxicology.94 (10):3449–3460.Bibcode:2020ArTox..94.3449P.doi:10.1007/s00204-020-02836-w.hdl:1854/LU-8687071.PMID32627074.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages. See also:Receptor/signaling modulators
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