2,5-Dimethoxy-4-bromoamphetamine

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INNTooltip International Nonproprietary Name)^[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.^[3]

Dimethoxybromoamphetamine
INN: Brolamfetamine

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; 4-Bromo-2,5-dimethoxyphenyl-isopropylamine
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule I UK: Class A US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
CAS Number	64638-07-9 Y  (racemate) 43061-15-0 (R-isomer) 43061-16-1 (S-isomer)
PubChem CID	62065
PubChem SID	46507989
IUPHAR/BPS	155
DrugBank	DB01484 Y
ChemSpider	55902 Y
UNII	67WJC4Y2QY
KEGG	D12707
ChEMBL	ChEMBL6607 Y
CompTox Dashboard (EPA)	DTXSID5050428
Chemical and physical data
Formula	C11H16BrNO2
Molar mass	274.158 g·mol−1
3D model (JSmol)	Interactive image
Melting point	63–65 °C (145–149 °F) (207–208 °C hydrochloride)
SMILES CC(CC1=CC(=C(C=C1OC)Br)OC)N
InChI InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3 Y Key:FXMWUTGUCAKGQL-UHFFFAOYSA-N Y
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Chemistry

Tabs of DOB, confiscated by police in Concord, California in 2006.

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

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.^[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.

History

DOB was first synthesized by Alexander Shulgin in 1967.^[3] It was first described in the scientific literature in a paper by Shulgin, Claudio Naranjo, and another colleague in 1971.^[4] The INNTooltip International Nonproprietary Name 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.^[15]

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

References

1. Anvisa (24 July 2023). "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 25 July 2023). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. World Health Organization (2000). International Nonproprietary Names (INN) for Pharmaceutical Substances. World Health Organization. ISBN 978-0-11-986227-0.
3. Erowid Online Books: "PiHKAL" - #62 DOB
4. 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.
5. 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.
6. 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.
7. 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.
8. Shulgin A (3 May 2005). "Ask Dr. Shulgin Online: DOB and Other Possible Prodrugs". Retrieved 2009-11-18.
9. 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.
10. "INN Proposed List 55". World Health Organization (WHO). 9 April 1986. Retrieved 2024-11-03.
11. "INN Recommended List 26". World Health Organization (WHO). 9 June 1986. Retrieved 2024-11-03.
12. World Health Organization (2024). "Use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances, 2024" (PDF). World Health Organization. pp. 152–153. Retrieved 2024-10-21.
13. "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2007-03-02. Retrieved 2007-03-30.
14. "(15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine)". Isomer Design. Archived from the original on 2021-11-23.
15. Department of Health and Aged Care (October 2015). "Poisons Standard". Federal Register of Legislation. Australian Government.
16. "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).
17. Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. p. 102. ISBN 978-0-9630096-3-0.
18. Bartels Jr JR (14 September 1973). "Part 308 – Schedules of Controlled Substances; Additions to Schedule I" (PDF). Federal Register. Vol. 38, no. 183. Drug Enforcement Administration. pp. 26447–8. Archived from the original (PDF) on 2022-03-03. Retrieved 2023-09-30 – via Isomer Design.

External links

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