2,5-dimethoxy-4-methylamphetamine

Structural formula
1: 1 mixture of enantiomers : ( R ) shape (left) and ( S ) shape (right)
General
Surname	2,5-dimethoxy-4-methylamphetamine
other names	1- (2,5-Dimethoxy-4-methylphenyl) propan-2-amine Dimethoxymethylamfetamine DOM STP
Molecular formula	C 12 H 19 NO 2
Brief description	white solid (hydrochloride)
External identifiers / databases
CAS number 15588-95-1 ( racemate ) 43061-13-8 [( R ) -form] 43061-14-9 [( S ) form] 15589-00-1 ( hydrochloride ) PubChem 85875 ChemSpider 77462 DrugBank DB01528 Wikidata Q62267185
properties
Molar mass	209.16 g mol −1
Physical state	firmly
Melting point	61 ° C (base) 189–190 ° C (hydrochloride)
safety instructions
GHS hazard labeling no classification available
Toxicological data	200 mg kg −1 ( LD 50 ,  rabbit ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,5-Dimethoxy-4-methylamphetamine (DOM) is a fully synthetic hallucinogen and belongs to the group of amphetamines .

history

DOM is a long and powerful psychedelic that was first made by Alexander Shulgin in 1964 . The name STP initially used for the substance probably comes from the motor oil brand of the same name, STP , since at the time various psychedelic phenethylamines were synthesized in the Pharmaceutical Chemistry Department of the University of California, San Francisco (UCSF) and labeled with motor oil names for unknown reasons. In mid-1967 DOM was generously distributed under the name STP in Haight-Ashbury , San Francisco , the tablets presumably came from the production of Owsley Stanley . These STP tablets contained 20 mg (later 10 mg) DOM. Due to the very late onset of the effect, many consumers followed up and then had an even stronger effect when the effect started, which also lasted for a very long time (up to 20 hours). Some consumers may have consumed 30 mg and more DOM in this way, with 10 mg already developing the full spectrum of action. At the time, it was not known that the substance in circulation was DOM. That was the reason why doctors in the emergency rooms were unable to help those affected with overdoses.

synthesis

A possible synthetic route is described in PIHKAL . The starting material 2,5-dimethoxy-4-methylbenzaldehyde is condensed with nitroethane to give the corresponding nitropropene and then reduced to the end product using lithium aluminum hydride .

Pharmacological properties

Pharmacokinetics

DOM is effective orally in doses of 3–10 mg, the duration of action is 14–20 hours. Since the effect is clearly noticeable only after 1.5–2 hours, the risk of overdosing is particularly high.

effect

DOM seems to have an amphetamine- like, disinhibiting and emotion-enhancing effect. In addition, many consumers report increased color perception and visual impressions that tend to synaesthesia with music. Some users speak of an entheogenic effect. DOM acts, among other things, as an agonist of the serotonin receptors 5-HT _2A / _2C .

DOM quickly leads to tolerance .

Like many other psychoactive substances, DOM also carries the risk of triggering a latent psychosis. The experience can be physically uncomfortable due to palpitations, tremors and overstimulation . Since DOM is dosed extremely low and the effect occurs quite late, there is a risk of unwanted overdosing and the associated particularly strong unpleasant side effects.

Narcotics regulations

DOM was introduced by the Narcotics Control Council of the UN in Schedule I of the Convention on Psychotropic Substances and is therefore practically illegal worldwide.

In the Federal Republic of Germany , DOM in 1971 was assimilated to the substances mentioned in Section 1 (1) No. 1 (b) of the Opium Act . As part of the replacement of the Opium Act by the Narcotics Act , it was classified as a non-marketable narcotic. For February 1998, the official spelling of was Dimethoxymethylamphetamin the German Narcotics Act in conformity with the WHO nomenclature in Dimethoxymethylamfetamin changed.

See also

• other dimethoxyamphetamines

literature

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

Web links

• DOM . In: Erowid . (English)

Individual evidence

1. ↑ ^{a b c} Alexander Shulgin, PHIKAL , p. 641f.
2. ↑ ^{a b} Entry on 2,5-dimethoxy-4-methylamphetamine. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ Entry on 2,5-dimethoxy-4-methylamphetamine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
5. ↑ erowid.org: DOM , accessed December 29, 2014.
6. ↑ www.erowid.org # 68 DOM , from: Alexander Shulgin, Ann Shulgin: PIHKAL - A Chemical Love Story. Transform Press, Berkeley 1995.
7. ↑ 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 .
8. ^ Fifth Narcotics Equal Opportunities Ordinance (5th BtMGLV) of April 6, 1971 ( Federal Law Gazette 1971 I p. 315); available at Eve & Rave : online
9. ↑ Appendix I to Section 1 of the BtMG
10. ↑ Tenth ordinance amending the provisions of the law on narcotics (10th BtMÄndV) of January 20, 1998 ( BGBl. I p. 74); available at Eve & Rave : PDF

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !