2,5-dimethoxy-4-methylphenylethylamine

Structural formula
General
Surname	2,5-dimethoxy-4-methylphenylethylamine
other names	2- (2,5-dimethoxy-4-methylphenyl) ethanamine ( IUPAC ); 2C-D; LE-25;
Molecular formula	C 11 H 17 NO 2
Brief description	white crystals (hydrochloride)
External identifiers / databases
PubChem	135740
ChemSpider	119559
Wikidata	Q209260
properties
Molar mass	195.26 g mol −1
Physical state	firmly
Melting point	213-214 ° C (hydrochloride)
solubility	good in ethanol , acetonitrile and isopropanol
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	80 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,5-dimethoxy-4-methylphenylethylamin (also abbreviated 2C-D ) is a psychedelic effective hallucinogen , which due to its structure to the substance groups of the phenol (including alkyl aryl ether ) of phenethylamine , and the 2Cs counts. The substance was developed in 1970 by a group at the Texas Research Institute of Mental Sciences . The American pharmacologist Alexander Shulgin then described the synthesis and effects on humans in his book PiHKAL . Among other things, 2C-D acts as a potent agonist of the serotonin receptors 5-HT _2A / _2C . 2C-D was used under Hanscarl Leuner in psycholytic psychotherapy as LE-25.

Legal status

In Germany, 2C-D has been subject to the Narcotics Act since the 28th ordinance amending the regulations on narcotics.

literature

Pablo R. Moya, Kelly A. Berg, Manuel A. Gutiérrez-Hernandez, Patricio Sáez-Briones, Miguel Reyes-Parada, Bruce K. Cassels, William P. Clarke: "Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives at Human 5- Hydroxytryptamine (5-HT) _2A and 5-HT _2C Receptors ", in: Journal of Pharmacology and Experimental Therapeutics , 2007 , 321 (3) , 1054-1061; doi: 10.1124 / jpet.106.117507 .
Robert T. Standridge, Henry G. Howell, Jonas A. Gylys, Richard A. Partyka, Alexander T. Shulgin: "Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1- (2,5-dimethoxy-4-methylphenyl ) butane ", in: Journal of Medicinal Chemistry , 1976 , 19 (12) , 1400-1404; doi: 10.1021 / jm00234a010 .
Beng-Thong Ho, L. Wayne Tansey, Robert L. Balster, Rong An, William M. McIsaac, Robert T. Harris: "Amphetamine analogs. II. Methylated phenethylamines", in: Journal of Medicinal Chemistry , 1970 , 13 (1 ) , 134-135; doi: 10.1021 / jm00295a034 .

Web links

2C-D . In: Erowid . (English)
isomerdesign.com: 2C-D (English)

Individual evidence

↑ ^a ^b ^c PiHKAL # 23 2C-D
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on 2,5-dimethoxy-4-methyl-phenethylamine in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
↑ Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT: Amphetamine analogs. II. Methylated phenethylamines . In: Journal of Medicinal Chemistry . 13, No. 1, January 1970, pp. 134-5. doi : 10.1021 / jm00295a034 . PMID 5412084 .
↑ CA Villalobos, P. Bull, P. Sáez, BK Cassels, JP Huidobro-Toro: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT _2A receptor antagonists in Xenopus laevis oocytes , in: Br. J. Pharmacol. , 2004 , 141 (7) , 1167-1174; PMC 1574890 (free full text).
↑ Pablo R. Moya, Kelly A. Berg, Manuel A. Gutiérrez-Hernandez, Patricio Sáez-Briones, Miguel Reyes-Parada, Bruce K. Cassels, William P. Clarke: "Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives in Human 5 -Hydroxytryptamine (5-HT) _2A and 5-HT _2C Receptors ", in: Journal of Pharmacology and Experimental Therapeutics , 2007 , 321 (3) , 1054-1061; doi: 10.1124 / jpet.106.117507 .
^ Peyton Jacob III and Alexander T. Shulgin: Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs ( Memento of July 23, 2015 in the Internet Archive ). In: NIDA Research Monograph 146: Hallucinogens: An Update. Pp. 74, 1994, United States Department of Health and Human Services.
↑ Erowid Character Vaults: Hanscarl Leuner
^ DG Addiction Medicine (PDF).

[pihkal-1] PiHKAL # 23 2C-D

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Entry on 2,5-dimethoxy-4-methyl-phenethylamine in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.

[pmid5412084-4] Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT: Amphetamine analogs. II. Methylated phenethylamines . In: Journal of Medicinal Chemistry . 13, No. 1, January 1970, pp. 134-5. doi : 10.1021 / jm00295a034 . PMID 5412084 .

[pubmed-5] CA Villalobos, P. Bull, P. Sáez, BK Cassels, JP Huidobro-Toro: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT _2A receptor antagonists in Xenopus laevis oocytes , in: Br. J. Pharmacol. , 2004 , 141 (7) , 1167-1174; PMC 1574890 (free full text).

[6] Pablo R. Moya, Kelly A. Berg, Manuel A. Gutiérrez-Hernandez, Patricio Sáez-Briones, Miguel Reyes-Parada, Bruce K. Cassels, William P. Clarke: "Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives in Human 5 -Hydroxytryptamine (5-HT) _2A and 5-HT _2C Receptors ", in: Journal of Pharmacology and Experimental Therapeutics , 2007 , 321 (3) , 1054-1061; doi: 10.1124 / jpet.106.117507 .

[7] Peyton Jacob III and Alexander T. Shulgin: Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs ( Memento of July 23, 2015 in the Internet Archive ). In: NIDA Research Monograph 146: Hallucinogens: An Update. Pp. 74, 1994, United States Department of Health and Human Services.

[8] Erowid Character Vaults: Hanscarl Leuner

[9] DG Addiction Medicine (PDF).