2,5-Dimethoxy-4-bromoamphetamine explained

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine ^[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.

Chemistry

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.

Pharmacology

Pharmacodynamics

DOB is a serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor agonist or partial agonist.^[6] Its psychedelic effects are mediated by its agonistic properties at the 5-HT_2A 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.^[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.

History

DOB was first synthesized by Alexander Shulgin in 1967. It was first described in the scientific literature in a paper by Shulgin, Claudio Naranjo, and another colleague in 1971. The of DOB, brolamfetamine, was proposed and recommended by the World Health Organization in 1986.^{[10] [11]} It was registered with the organization as a supposed "anorexic" (appetite suppressant).^[12]

Legal status

Internationally, DOB is a Schedule I substance under the Convention on Psychotropic Substances and the drug is legal only for medical, industrial or scientific purposes.^[13]

Canada

Listed as a Schedule 1 as it is an analogue of amphetamine.^[14]

Australia

DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).^[15] 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.

Russia

Schedule I, possession of at least 10 mg is a criminal offence.^[16]

United Kingdom

DOB is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971.

United States

DOB is a Schedule I controlled substance under federal law in the United States.^[17] It was scheduled in 1973.^[18]

See also

• 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

External links

• DOB Entry in PiHKAL
• DOB Entry in PiHKAL • info
• Erowid DOB Vault

Notes and References

1. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
2. Book: World Health Organization. International Nonproprietary Names (INN) for Pharmaceutical Substances. 2000. World Health Organization. 978-0-11-986227-0.
3. http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml Erowid Online Books: "PiHKAL" - #62 DOB
4. Shulgin AT, Sargent T, Naranjo C . 4-Bromo-2,5-dimethoxyphenylisopropylamine, a new centrally active amphetamine analog . Pharmacology . 5 . 2 . 103–107 . 1971 . 5570923 . 10.1159/000136181 . 46844380 .
5. Parrish JC, Braden MR, Gundy E, Nichols DE . Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists . Journal of Neurochemistry . 95 . 6 . 1575–1584 . December 2005 . 16277614 . 10.1111/j.1471-4159.2005.03477.x . 24005602 . free .
6. Ray TS . Psychedelics and the human receptorome . PLOS ONE . 5 . 2 . e9019 . February 2010 . 20126400 . 2814854 . 10.1371/journal.pone.0009019 . free . 2010PLoSO...5.9019R .
7. Lewin AH, Miller GM, Gilmour B . Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class . Bioorganic & Medicinal Chemistry . 19 . 23 . 7044–7048 . December 2011 . 22037049 . 3236098 . 10.1016/j.bmc.2011.10.007 .
8. Web site: Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs . 18 November 2009 . Shulgin A . 2005-05-03.
9. Bowen JS, Davis GB, Kearney TE, Bardin J . Diffuse vascular spasm associated with 4-bromo-2,5-dimethoxyamphetamine ingestion . JAMA . 249 . 11 . 1477–1479 . March 1983 . 6827726 . 10.1001/jama.1983.03330350053028 .
10. Web site: INN Proposed List 55 . World Health Organization (WHO) . 9 April 1986 . . 3 November 2024.
11. Web site: INN Recommended List 26 . World Health Organization (WHO) . 9 June 1986 . . 3 November 2024.
12. Web site: ((World Health Organization)) . Use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances, 2024 . World Health Organization . 2024 . 21 October 2024 . 152–153.
13. Web site: List of psychotropic substances under international control . 30 March 2007 . https://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf . 2 March 2007 . dead .
14. Web site: (15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine) . https://web.archive.org/web/20211123123506/http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=1&structure=C . 2021-11-23 . Isomer Design .
15. Web site: Department of Health and Aged Care . Federal Register of Legislation . Australian Government . Poisons Standard . October 2015 .
16. Web site: 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 . Постановление Правительства РФ от 01.10.2012 N 1002 . Resolution of the Government of the Russian Federation of 01.10.2012 N 1002 . 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 . ru .
17. Book: Shulgin A, Manning T, Daley PF . The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Transform Press . Berkeley . 1 . 2011 . 978-0-9630096-3-0 . 102 . 2 November 2024.
18. Bartels Jr JR . September 14, 1973 . Part 308 – Schedules of Controlled Substances; Additions to Schedule I . Federal Register . 38 . 183 . 26447–8 . . September 30, 2023 . Isomer Design . https://web.archive.org/web/20220303023114/https://isomerdesign.com/Cdsa/FR/38FR26447.pdf . March 3, 2022.