2,5-Dimethoxy-4-bromoamphetamine

Last updated

Dimethoxybromoamphetamine
INN: Brolamfetamine
DOB-racemic-skeletal.svg
Chemical structure of (±)-DOB
DOB-3d-sticks.png
Ball-and-stick model of (R)-DOB
Clinical data
Other namesDOB; 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
Identifiers
  • 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
PubChemSID
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)
  • CC(CC1=CC(=C(C=C1OC)Br)OC)N
  • 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 Yes check.svgY
  • Key:FXMWUTGUCAKGQL-UHFFFAOYSA-N Yes check.svgY
   (verify)

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN Tooltip 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]

Contents

The drug acts as a serotonin 5-HT2 receptor agonist. [5] [6]

Chemistry

Tabs of DOB, confiscated by police in Concord, California in 2006. DOB blotters.jpg
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, [7] 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 ]

Side effects

Excessively high doses of DOB may cause diffuse arterial spasm. [8] The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline. [8]

Pharmacology

Pharmacodynamics

DOB activities
Target Affinity (Ki, nM)
5-HT1A 2,550–6,327
5-HT1B 941
5-HT1D 636
5-HT1E 556–1,427
5-HT1F ND
5-HT2A 0.6–81 (Ki)
0.52–0.93 (EC50 Tooltip half-maximal effective concentration)
89–97% (Emax Tooltip maximal efficacy)
5-HT2B 2.9–44
5-HT2C 1.3–60 (Ki)
0.25–0.31 (EC50)
95–112% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 5,311
5-HT6 5,535
5-HT7 506
α1A, α1B >10,000
α1D ND
α2A 4,266
α2B 1,527
α2C 594
β1 2,425
β2 303
D1, D2 >10,000
D3 808
D4, D5 >10,000
H1 9,120
H2–H4 >10,000
M1, M2 >10,000
M3 1,152
M4, M5 >10,000
TAAR1 >1,000
I1 1,596
σ1 2,193
σ2 >10,000
SERT Tooltip Serotonin transporter8,538 (Ki)
NET Tooltip Norepinephrine transporter>10,000 (Ki)
DAT Tooltip Dopamine transporter>10,000 (Ki)
MAO-A Tooltip Monoamine oxidase A100,000 (IC50 Tooltip half-maximal inhibitory concentration) (rat)
MAO-B Tooltip Monoamine oxidase B>100,000 (IC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [9] [10] [5] [11] [12] [13] [6] [14]

DOB is a serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist. [5] [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 a very weak agonist of the human trace amine-associated receptor 1 (TAAR1) and a weak agonist of the rhesus monkey TAAR1. [14] [6] In contrast to the serotonin releasing agent MDMA, DOB does not produce protein kinase C (PKC) activation in the brains of rodents in vivo . [15] [16] The PKC activation by MDMA appears to be dependent on uptake by the serotonin transporter (SERT). [15] [16]

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 INN Tooltip International Nonproprietary Name of DOB, brolamfetamine, was proposed and recommended by the World Health Organization (WHO) in 1986. [17] [18] This was the same year that the Multidisciplinary Association for Psychedelic Studies (MAPS) was founded. [19] DOB was registered with the WHO as a supposed "anorexic" (appetite suppressant). [20]

Society and culture

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. [21]

Canada

Listed as a Schedule 1 as it is an analogue of amphetamine. [22]

Australia

DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017). [23] 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. [23]

Russia

Schedule I, possession of at least 10 mg is a criminal offence. [24]

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. [25] It was scheduled in 1973. [26]

See also

Related Research Articles

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<span class="mw-page-title-main">2,4,5-Trimethoxyamphetamine</span> Pharmaceutical compound

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<span class="mw-page-title-main">2,5-Dimethoxy-4-chloroamphetamine</span> Chemical compound

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<span class="mw-page-title-main">4C-B</span> Chemical compound

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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. 1 2 3 Erowid Online Books: "PiHKAL" - #62 DOB
  4. 1 2 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. 1 2 3 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.
  6. 1 2 3 4 Rudin D, Luethi D, Hoener MC, Liechti ME (2022). "Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues". The FASEB Journal. 36 (S1). doi: 10.1096/fasebj.2022.36.S1.R2121 . ISSN   0892-6638.
  7. ↑ 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.
  8. 1 2 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.
  9. ↑ "PDSP Database". UNC (in Zulu). Retrieved 2025-02-04.
  10. ↑ Liu T. "BindingDB BDBM50005257 (+)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(+/-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)-2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::(-)2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine::2-(2-Methoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((R)-(-)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine((S)-(+)-DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(DOB)::2-(4-Bromo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[R(-)DOB]::2-(5-Bromo-2,4-dimethoxy-phenyl)-1-methyl-ethylamine::Brolamfetamine::CHEMBL6607::DOB::Racemic DOB". BindingDB. Retrieved 2025-02-04.
  11. ↑ van Wijngaarden I, Soudijn W (1997). "5-HT2A, 5-HT2B and 5-HT2C receptor ligands". Pharmacochemistry Library. Vol. 27. Elsevier. pp. 161–197. doi:10.1016/s0165-7208(97)80013-x. ISBN   978-0-444-82041-9.
  12. ↑ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi: 10.3389/fphar.2019.01590 . PMC   6989591 . PMID   32038257.
  13. ↑ Scorza MC, Carrau C, Silveira R, Zapata-Torres G, Cassels BK, Reyes-Parada M (December 1997). "Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives: structure-activity relationships". Biochem Pharmacol. 54 (12): 1361–1369. doi:10.1016/s0006-2952(97)00405-x. PMID   9393679.
  14. 1 2 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.
  15. 1 2 Kramer HK, Poblete JC, Azmitia EC (September 1997). "Activation of protein kinase C (PKC) by 3,4-methylenedioxymethamphetamine (MDMA) occurs through the stimulation of serotonin receptors and transporter". Neuropsychopharmacology. 17 (3): 117–129. doi:10.1016/S0893-133X(97)00026-2. PMID   9272479.
  16. 1 2 Kenneth H (1996). "Evidence for the involvement of the serotonin uptake transporter and the serotonin-2 receptor in the activation of protein kinase C (PKC) by substituted amphetamines in the adult rodent brain". ProQuest. New York University. Retrieved 2025-02-01. MDMA manifests its acute psychotropic and neurotoxic effects by releasing 5-HT from nerve endings. MDMA also shows a moderate agonist-like affinity (1.5-3.2 mM [(sic)]) for the central 5-HT2 receptor. Activation of this receptor stimulates the translocation/activation of protein kinase C (PKC) and the release of Ca2+ from intracellular sequestration sites. MDMA has already been shown to increase [Ca2+], and this may proceed through the activation of this receptor. [...] In vivo, both MDMA and PCA were found to produce a lasting translocation of [protein kinase C (PKC)] in the cortex and hippocampus of treated rats. Fluoxetine, a 5-HT uptake inhibitor, prevents PKC translocation, while ketanserin, a 5-HT2A antagonist, acts similarly but a diminished efficacy. Non-neurotoxic drugs like fluoxetine, DOB, and cocaine were devoid of MDMA's long-term PKC translocating abilities, and suggests that receptor stimulation alone is not the sole mechanism. In synaptosomes, MDMA was effective at producing PKC translocation by binding to the 5-HT uptake carner. This in vitro response [of] fluoxetine reverses this response and demonstrates that MDMA translocates PKC within in the 5-HT nerve terminal.
  17. ↑ "INN Proposed List 55". World Health Organization (WHO). 9 April 1986. Retrieved 2024-11-03.
  18. ↑ "INN Recommended List 26". World Health Organization (WHO). 9 June 1986. Retrieved 2024-11-03.
  19. ↑ Emerson A, Ponté L, Jerome L, Doblin R (2014). "History and future of the Multidisciplinary Association for Psychedelic Studies (MAPS)". J Psychoactive Drugs. 46 (1): 27–36. doi:10.1080/02791072.2014.877321. PMID   24830183.
  20. ↑ 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.
  21. ↑ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2007-03-02. Retrieved 2007-03-30.
  22. ↑ "(15) 4-Bromo-2,5-dimethoxyamphetamine (4-Bromo-2,5-dimethoxy-α-methylbenzeneethanamine)". Isomer Design. Archived from the original on 2021-11-23.
  23. 1 2 Department of Health and Aged Care (October 2015). "Poisons Standard". Federal Register of Legislation. Australian Government.
  24. ↑ "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).
  25. ↑ 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.
  26. ↑ 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.
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