Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN)[2] and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967.[3][4] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.
 Chemical structure of (±)-DOB | |
 Ball-and-stick model of (R)-DOB | |
| Clinical data | |
|---|---|
| Other names | DOB; 4-Bromo-2,5-dimethoxyamphetamine; Brolamfetamine; Brolamphetamine; Bromo-DMA; 2,5-Dimethoxy-4-bromo-α-methylphenethylamine |
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number |
|
| PubChem CID | |
| PubChem SID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H16BrNO2 |
| Molar mass | 274.158 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 63–65 °C (145–149 °F) (207–208 °C hydrochloride) |
| |
| |
| (verify) | |
Chemistry
edit
The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(−)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[5] making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.[citation needed]
Pharmacology
editDOB is a 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist or partial agonist.[6] Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. It is an agonist of human TAAR1.[7]
It has been suggested that DOB is a prodrug metabolized in the lungs.[3][8]
Excessively high doses of this hallucinogen may cause diffuse arterial spasm.[9] The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.
Legal status
editInternationally, DOB is a Schedule I substance under the Convention on Psychotropic Substances and the drug is legal only for medical, industrial or scientific purposes.[10]
Canada
editListed as a Schedule 1 as it is an analogue of amphetamine.[11]
Australia
editDOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[12] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[12]
Russia
editSchedule I, possession of at least 10 mg is a criminal offence.[13]
United Kingdom
editDOB is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971.
See also
edit- 2,5-Dimethoxy-4-substituted amphetamines
- 2C-B – the α-desmethyl derivative of DOB
- 4C-B – the α-ethyl homologue of DOB
- β-Methyl-2C-B
- DOB-FLY
References
edit- ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ World Health Organization (2000). International Nonproprietary Names (INN) for Pharmaceutical Substances. World Health Organization. ISBN 978-0-11-986227-0.
- ^ a b Erowid Online Books: "PiHKAL" - #62 DOB
- ^ Shulgin AT, Sargent T, Naranjo C (1971). "4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog". Pharmacology. 5 (2): 103–107. doi:10.1159/000136181. PMID 5570923. S2CID 46844380.
- ^ Parrish JC, Braden MR, Gundy E, Nichols DE (December 2005). "Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists". Journal of Neurochemistry. 95 (6): 1575–1584. doi:10.1111/j.1471-4159.2005.03477.x. PMID 16277614. S2CID 24005602.
- ^ Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
- ^ Lewin AH, Miller GM, Gilmour B (December 2011). "Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class". Bioorganic & Medicinal Chemistry. 19 (23): 7044–7048. doi:10.1016/j.bmc.2011.10.007. PMC 3236098. PMID 22037049.
- ^ Shulgin A (2005-05-03). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". Retrieved 18 November 2009.
- ^ Bowen JS, Davis GB, Kearney TE, Bardin J (March 1983). "Diffuse vascular spasm associated with 4-bromo-2,5-dimethoxyamphetamine ingestion". JAMA. 249 (11): 1477–1479. doi:10.1001/jama.1983.03330350053028. PMID 6827726.
- ^ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2 March 2007. Retrieved 30 March 2007.
- ^ "(15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine)". Isomer Design. Archived from the original on 2021-11-23.
- ^ a b Department of Health and Aged Care (October 2015). "Poisons Standard". Federal Register of Legislation. Australian Government.
- ^ "Об утверждении значительного, крупного и особо крупного размеров наркотических средств и психотропных веществ, а также значительного, крупного и особо крупного размеров для растений, содержащих наркотические средства или психотропные вещества, либо их частей, содержащих наркотические средства или психотропные вещества, для целей статей 228, 228.1, 229 и 229.1 Уголовного кодекса Российской Федерации" [On approval of significant, large and especially large sizes of narcotic drugs and psychotropic substances, as well as significant, large and especially large sizes for plants containing narcotic drugs or psychotropic substances, or their parts containing narcotic drugs or psychotropic substances, for the purposes of Articles 228, 228.1, 229 and 229.1 of the Criminal Code of the Russian Federation]. Постановление Правительства РФ от 01.10.2012 N 1002 [Resolution of the Government of the Russian Federation of 01.10.2012 N 1002] (in Russian).