2,5-dimethoxy-4-iodophenethylamine

Structural formula
General
Surname	2,5-dimethoxy-4-iodophenethylamine
other names	2- (4-iodo-2,5-dimethoxyphenyl) ethanamine ( IUPAC ); 2C-I; 4-iodo-2,5-dimethoxyphenethylazane;
Molecular formula	C 10 H 14 INO 2
Brief description	white crystals (hydrochloride)
External identifiers / databases
EC number	690-397-2
ECHA InfoCard	100.217.507
PubChem	10267191
ChemSpider	8442670
Wikidata	Q209255
properties
Molar mass	307.13 g mol −1
Physical state	firmly
Melting point	246 ° C (hydrochloride)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

One 2C-I tablet

2,5-Dimethoxy-4-iodophenethylamine (abbreviated 2C-I ) is a psychedelic , which, due to its structure, belongs to the substance groups of phenol ethers , phenethylamines , as well as to the substance group of 2Cs .

history

The American chemist Alexander Shulgin synthesized 2C-I for the first time and mentions synthesis, dose and effect in his book PiHKAL .

Pharmacodynamics

The effect is described as stimulating , entactogenic / empathogenic and entheogenic , among other things . This is attributed, among other things, to the mode of action of the 2C-Is as a potent agonist of the serotonin receptors 5-HT _2A / _2C . 2C-I acts (among other things) as a serotonin-noradrenaline reuptake inhibitor (IC ₅₀ 5-HT: 79 ± 19 μM NE: 37 ± 12 μM).

Pharmacokinetics

Shulgin specifies the orally effective dose in the range from 14 to 22 mg, the duration of action as 6-10 hours.

Legal status

2C-I is a non-marketable narcotic drug in the Federal Republic of Germany due to its listing in Appendix I BtMG . Handling without permission is generally a criminal offense.

literature

Alexander Shulgin, Ann Shulgin: PIHKAL - A Chemical Love Story Transform Press, ISBN 0-9630096-0-5 .

Web links

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

Individual evidence

↑ ^a ^b ^c ^d PiHKAL # 33 2C-I
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 16, 2020, is derived from a self-classification by the distributor .
↑ 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 .
↑ F. Nagai, R. Nonaka, K. Satoh Hisashi Kamimura: The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. In: European journal of pharmacology. Volume 559, Number 2-3, March 2007, pp. 132-137, doi : 10.1016 / j.ejphar.2006.11.075 . PMID 17223101 .

[pihkal-1] PiHKAL # 33 2C-I

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A label of [No public or meaningful name is available] in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 16, 2020, is derived from a self-classification by the distributor .

[pubmed-3] 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).

[4] 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 .

[PMID17223101-5] F. Nagai, R. Nonaka, K. Satoh Hisashi Kamimura: The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. In: European journal of pharmacology. Volume 559, Number 2-3, March 2007, pp. 132-137, doi : 10.1016 / j.ejphar.2006.11.075 . PMID 17223101 .