4-Bromomescaline

4-Bromomescaline
Clinical data
Other names	3,5-Dimethoxy-4-bromophenethylamine; 4-Bromo-3,5-dimethoxyphenethylamine; 4-Br-3,5-DMPEA; 3,4,5-MBM
Routes of; administration	Unknown
Drug class	Serotonin receptor modulator
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 2-(4-bromo-3,5-dimethoxyphenyl)ethanamine;
CAS Number	61367-72-4;
PubChem CID	15102778;
ChemSpider	10438341;
ChEMBL	ChEMBL3305574;
CompTox Dashboard (EPA)	DTXSID50876055 ;
Chemical and physical data
Formula	C10H14BrNO2
Molar mass	260.131 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=CC(=C1Br)OC)CCN;
	InChI InChI=1S/C10H14BrNO2/c1-13-8-5-7(3-4-12)6-9(14-2)10(8)11/h5-6H,3-4,12H2,1-2H3; Key:DQTTUBZTFBEBCK-UHFFFAOYSA-N;

4-Bromomescaline, also known as 4-bromo-3,5-dimethoxyphenethylamine (4-Br-3,5-DMPEA), is a serotonin receptor modulator of the phenethylamine and scaline families related to the psychedelic drug mescaline.^[1]^[2] It is the analogue of mescaline in which the methoxy group at the 4 position has been replaced with a bromine atom.^[1]^[2] The drug is also the phenethylamine (α-desmethyl) analogue of 4-Br-3,5-DMA and a positional isomer of 2C-B (4-Br-2,5-DMPEA).^[1]^[2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin briefly mentions 4-bromomescaline and states that it has never been tested in humans.^[1] As such, its properties and effects in humans are unknown.^[1]

Pharmacology

Pharmacodynamics

4-Bromomescaline has been found to be a potent serotonin receptor agonist in the sheep umbilical artery (EC₅₀Tooltip half-maximal effective concentration = 185 nM).^[1]^[2]^[3] It was 7.6-fold more potent than mescaline in this assay.^[3] In a subsequent study, the drug showed high affinity for the serotonin 5-HT_2A receptor (K_0.5 = 45 nM).^[4] Its affinity for this receptor was approximately 18-fold higher than that of mescaline.^[4]

Chemistry

Analogues

Analogues of 4-bromomescaline include mescaline, desoxy (4-desoxymescaline; 4-methylmescaline; 4-Me-3,5-DMPEA), 4-O-desmethylmescaline (desmethyl; 4-hydroxymescaline; 4-OH-3,5-DMPEA), 2C-B (4-Br-2,5-DMPEA), and 4-Br-3,5-DMA, among others.^[1]^[2]^[4] 4-Br-3,5-DMA has been found to be a potent psychoactive drug in humans, though it did not produce clear hallucinogenic effects at tested doses of 3 to 10 mg orally and instead produced pronounced analgesic and tactile anesthetic effects among others.^[1]^[5]^[6] On the other hand, desoxy (4-methylmescaline), a positional isomer of 2C-D, is a psychedelic drug similarly to mescaline at doses of 40 to 120 mg orally, albeit with distinct effects.^[1]^[2]

Daniel Trachsel has expressed great interest in scaline-related compounds of the formula 4-X-3,5-DMPEA without an oxygen atom at the 4 position like desoxy (4-methylmescaline; 4-Me-3,5-DMPEA) and 4-bromomescaline (4-Br-3,5-DMPEA).^[2] He has described a variety of theoretical compounds of this class that could be explored, such as desoxyescaline (DE; 4-ethylmescaline; 4-Et-3,5-DMPEA), desoxytrifluoromescaline (DTFM; 4-trifluoromethylmescaline; 4-TFM-3,5-DMPEA), desoxytrifluoroescaline (DTFE; 4-trifluoroethylmescaline; 4-TFE-3,5-TMPEA), desoxyproscaline (DPR; 4-propylmescaline; 4-Pr-3,5-TMPEA), desoxyallylescaline (DAL; 4-allylmescaline; 4-AL-3,5-TMPEA), and desoxymethallylescaline (DMAL; 4-methallylmescaline; 4-MeAL-3,5-TMPEA), among others.^[2]

History

4-Bromomescaline was first described in the scientific literature by David E. Nichols and Shulgin and colleagues in 1977.^[2]^[3]^[5] Subsequently, it was described by Shulgin in PiHKAL in 1991.^[1]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent amphetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, ~~3,5-dimethoxy-4-bromoamphetamine~~ 4-bromo-3,5-dimethoxyphenethylamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man."
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 740–744. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025. [Translated:] Compounds 154-155 contain a halogen atom instead of the 4-alkyloxy group found in many known mescaline analogues. 4-BR (154) was tested by Nichols and Dyer for the correlation between lipophilicity and 5-HT agonist activity [103]. The 3C analogue 4-BR-3,5-DMA (155) was described by Shulgin for its activity in humans [19]; at a dose of 4-10 mg, no significant effects were observed (a certain, undefined effect was present for 8-12 h), but there were indications of analgesic effects. However, these could not be confirmed in an animal study [19]. [...] Shulgin investigated the effects of desoxymescaline (DESOXY; 164) in humans [19]. He mentions a dosage of 40-120 mg and a duration of action of 6-8 hours. The psychedelic color display of mescaline (1) does not appear to be present; however, the imagery induced by music with closed eyes was clearly evident. The initial results from DESOXY (164) suggest that further interesting substances of this type are possible. What would other homo-scalines without the oxygen in the 4-position show in vitro and in vivo? The substance desoxyescalin (DE; 166) is, at least sterically speaking, closer to mescaline (1) than DESOXY (164). Many other potentially interesting deoxy compounds are conceivable, such as 167-174, and it would be quite exciting to have the in vitro and in vivo data at hand to learn more about the properties of the 3,4,5-trisubstituted phenylalkylamines. Here, too, 3C analogs would be conceivable, a currently completely unexplored class. What would happen if one of the two MeO groups in DESOXY (164) or in 166-174 were replaced by an EtO, MeS, or EtS substituent? This results in countless theoretical combinations!
^ ^a ^b ^c Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". Journal of Medicinal Chemistry. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.
^ ^a ^b ^c McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025 – via Purdue e-Pubs.
^ ^a ^b Nichols DE, Shulgin AT, Dyer DC (August 1977). "Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives". Life Sciences. 21 (4): 569–575. doi:10.1016/0024-3205(77)90099-6. PMID 904435.
^ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.5.7. 4-Bromo-3,5-dimethoxyphenylisopropylamine: 4-Bromo-3,5-dimethoxyphenylisopropylamine (85) has been prepared (Barfknecht and Nichols, 1971) and found to be centrally active in man (Nichols et al., 1977). Threshold effects are first noted in the dose range 3-6 mg, and at 10 mg orally there are indications of both mental (psychotomimetic?) and physical (central analgesia) effects. The action of the drug appears to be complex, and a single assignment of its character will have to await additional studies.

External links

4-Br-3,5-DMPEA - Isomer Design

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent amphetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, ~~3,5-dimethoxy-4-bromoamphetamine~~ 4-bromo-3,5-dimethoxyphenethylamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man."

[Trachsel_2013-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 740–744. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025. [Translated:] Compounds 154-155 contain a halogen atom instead of the 4-alkyloxy group found in many known mescaline analogues. 4-BR (154) was tested by Nichols and Dyer for the correlation between lipophilicity and 5-HT agonist activity [103]. The 3C analogue 4-BR-3,5-DMA (155) was described by Shulgin for its activity in humans [19]; at a dose of 4-10 mg, no significant effects were observed (a certain, undefined effect was present for 8-12 h), but there were indications of analgesic effects. However, these could not be confirmed in an animal study [19]. [...] Shulgin investigated the effects of desoxymescaline (DESOXY; 164) in humans [19]. He mentions a dosage of 40-120 mg and a duration of action of 6-8 hours. The psychedelic color display of mescaline (1) does not appear to be present; however, the imagery induced by music with closed eyes was clearly evident. The initial results from DESOXY (164) suggest that further interesting substances of this type are possible. What would other homo-scalines without the oxygen in the 4-position show in vitro and in vivo? The substance desoxyescalin (DE; 166) is, at least sterically speaking, closer to mescaline (1) than DESOXY (164). Many other potentially interesting deoxy compounds are conceivable, such as 167-174, and it would be quite exciting to have the in vitro and in vivo data at hand to learn more about the properties of the 3,4,5-trisubstituted phenylalkylamines. Here, too, 3C analogs would be conceivable, a currently completely unexplored class. What would happen if one of the two MeO groups in DESOXY (164) or in 166-174 were replaced by an EtO, MeS, or EtS substituent? This results in countless theoretical combinations!

[Nichols_1977-3] Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". Journal of Medicinal Chemistry. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.

[McCorvy_2013-4] McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025 – via Purdue e-Pubs.

[Nichols_1977a-5] Nichols DE, Shulgin AT, Dyer DC (August 1977). "Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives". Life Sciences. 21 (4): 569–575. doi:10.1016/0024-3205(77)90099-6. PMID 904435.

[Shulgin_1978-6] Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.5.7. 4-Bromo-3,5-dimethoxyphenylisopropylamine: 4-Bromo-3,5-dimethoxyphenylisopropylamine (85) has been prepared (Barfknecht and Nichols, 1971) and found to be centrally active in man (Nichols et al., 1977). Threshold effects are first noted in the dose range 3-6 mg, and at 10 mg orally there are indications of both mental (psychotomimetic?) and physical (central analgesia) effects. The action of the drug appears to be complex, and a single assignment of its character will have to await additional studies.

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