2,5-dimethoxy-4-bromamphetamine

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	2,5-dimethoxy-4-bromamphetamine
other names	1- (4-bromo-2,5-dimethoxyphenyl) -2-propanamine ( IUPAC ); ( RS ) -2,5-dimethoxy-4-bromamphetamine; Brolamfetamine ( INN ); DOB;
Molecular formula	C 11 H 16 BrNO 2
Brief description	white crystals (hydrochloride); white solid (hydrobromide);
External identifiers / databases
PubChem	62065
ChemSpider	55902
DrugBank	DB01484
Wikidata	Q209241
properties
Molar mass	274.15 g · mol -1 (base); 310.62 g · mol -1 (hydrochloride); 355.07 g · mol -1 (hydrobromide);
Physical state	firmly
Melting point	207-208 ° C (hydrochloride); 172-174 ° C (hydrobromide);
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 302-310-330
	P: 260-280-284-302 + 350-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,5-dimethoxy-4-bromamphetamine (abbr. DOB ) is a powerful psychedelic hallucinogen . Chemically it belongs to the amphetamine structural class .

Isomerism

2,5-Dimethoxy-4-bromamphetamine is chiral , hence there are two enantiomeric forms: ( R ) -2,5-Dimethoxy-4-bromamphetamine and ( S ) -2,5-Dimethoxy-4-bromamphetamine.

Isomers of 2,5-dimethoxy-4-bromoamphetamine
Surname	( R ) -2,5-dimethoxy-4-bromamphetamine	( S ) -2,5-dimethoxy-4-bromamphetamine
other names	(-) - 2,5-Dimethoxy-4-bromamphetamine	(+) - 2,5-dimethoxy-4-bromamphetamine
Structural formula
CAS number	43061-15-0 (base) 50505-92-5 ( hydrochloride ) 53581-79-6 ( hydrobromide )	43061-16-1 (base) 50505-93-6 ( hydrochloride ) 53581-80-9 ( hydrobromide )
	64638-07-9 (base, unspec.) 29705-96-2 (hydrochloride, unspec.) 53581-53-6 (hydrobromide, unspec.)
PubChem	12626561 (base)	23983765 (base)
	62065 (Base, unspec.)
DrugBank	-	-
	DB01484
Wikidata	Q27275334 (Base)	Q27285094 (Base)
	Q209241 (base, unspec.)

history

DOB was first synthesized in 1967 by Alexander Shulgin . The first reports on the effects and the unexpectedly high potency of DOB appeared in 1971.

synthesis

A possible synthetic route is described in PIHKAL by bromination of 2,5-dimethoxyamphetamine.

Pharmacological properties

Pharmacokinetics

Dimethoxybromamphetamine is already effective in doses of 1–3 mg and has a very long duration of action of 18–30 hours. The effect starts quite late.

The distribution and metabolism in the body was investigated using radioactively labeled DOB as a radioligand . The substance accumulates in the lungs over several hours and only later reaches the brain . This suggests that DOB is metabolized in the lungs and that only the metabolite is mainly psychoactive . This would explain both the late onset of action and the long duration of action.

effect

DOB seems u. a. to have an entactogenic effect and, above all, to strengthen the color perception and the sense of touch. Like many other psychoactive substances, DOB also harbors the risk of triggering a latent psychosis (see also HPPD ). In the case of unfavorable predispositions, even a “normal” dose can lead to an effect that is hardly controllable. High overdoses can lead to severe poisoning and symptoms of paralysis, and deaths have also been documented. Physical side effects such as tremors and cramps were already reported by users at the effective dose given above . Like other 2,5-dimethoxy-4-substituted amphetamines, DOB acts as an agonist of the serotonin receptors 5-HT _2A / _2C .

Narcotics regulations

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

In the Federal Republic of Germany, DOB was included in Annex I of the Narcotics Act in 1984 as a non-marketable narcotic drug . In February 1998 the official name of dimethoxybromamphetamine in the German Narcotics Act was changed to the international non-proprietary name (INN) brolamfetamine . 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

DOB in PIHKAL
DOB . In: Erowid . (English)

Individual evidence

↑ ^a ^b ^c PiHKAL # 62 DOB
↑ ^a ^b ^c ^d data sheet (±) -2,5-dimethoxy-4-bromoamphetamine hydrobromide from Sigma-Aldrich , accessed on December 22, 2011 ( PDF ).
↑ PIHKAL: # 62
^ Daniel Trachsel, Nicolas Richard: Psychedelische Chemie Nachtschatten, 2000, pp. 112 and 114.
↑ 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 .
^ First Narcotics Law Amendment Ordinance (1st BtMÄndV) of 6 August 1984 ( BGBl. 1984 I p. 1081); available at Eve & Rave : (PDF) .
↑ 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) .

[pihkal-1] PiHKAL # 62 DOB

[Sigma-2] ta sheet (±) -2,5-dimethoxy-4-bromoamphetamine hydrobromide from Sigma-Aldrich , accessed on December 22, 2011 ( PDF ).

[3] PIHKAL: # 62

[4] Daniel Trachsel, Nicolas Richard: Psychedelische Chemie Nachtschatten, 2000, pp. 112 and 114.

[5] 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 .

[6] First Narcotics Law Amendment Ordinance (1st BtMÄndV) of 6 August 1984 ( BGBl. 1984 I p. 1081); available at Eve & Rave : (PDF) .

[7] 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) .