2-Bromomescaline

2-Bromomescaline
Clinical data
ATC code	none;
Identifiers
	IUPAC name 2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine;
CAS Number	37015-19-3 ;
PubChem CID	16637783;
ChemSpider	17574207 ;
UNII	A9M89XG7QW;
CompTox Dashboard (EPA)	DTXSID301032900 ;
Chemical and physical data
Formula	C11H16BrNO3
Molar mass	290.157 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C(=C(C(=C1)CCN)Br)OC)OC;
	InChI InChI=1S/C11H16BrNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3; Key:UXQBKANLBLUVMK-UHFFFAOYSA-N;

2-Bromomescaline (2-Br-M) is a derivative of the phenethylamine hallucinogen mescaline which has an unusual 2-bromo substitution.^[1]^[2] It is an agonist for serotonin receptors, with a binding affinity of 215 nM at 5-HT_1A, 513 nM at 5-HT_2A and 379 nM at 5-HT_2C, so while it is around ten times more tightly binding than mescaline at 5-HT_1A and 5-HT_2A receptors, it is over twenty times more potent at 5-HT_2C.^[3] It has been reported as a designer drug, first identified in Austria in January 2023.^[4]

References

^ Shulgin A, Manning T, Daley PF (2011). The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press. pp. 280–281, 355. ISBN 978-0-9630096-3-0.
^ Pecherer B, Sunbury RC, Brossi A (June 1972). "A novel synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5-tetrahydro-1H3-benzazepines". Journal of Heterocyclic Chemistry. 9 (3): 609–616. doi:10.1002/jhet.5570090322.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 908–910. ISBN 978-3-03788-700-4.
^ "New psychoactive substances - the current situation in Europe" (PDF). European Drug Report. European Union Drugs Agency (EUDA). 2024.

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[1] Shulgin A, Manning T, Daley PF (2011). The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press. pp. 280–281, 355. ISBN 978-0-9630096-3-0.

[2] Pecherer B, Sunbury RC, Brossi A (June 1972). "A novel synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5-tetrahydro-1H3-benzazepines". Journal of Heterocyclic Chemistry. 9 (3): 609–616. doi:10.1002/jhet.5570090322.

[3] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 908–910. ISBN 978-3-03788-700-4.

[4] "New psychoactive substances - the current situation in Europe" (PDF). European Drug Report. European Union Drugs Agency (EUDA). 2024.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Clinical data

ATC code	none
Identifiers
IUPAC name 2-(2-Bromo-3,4,5-trimethoxyphenyl)ethanamine
CAS Number	37015-19-3^Y
PubChem CID	16637783
ChemSpider	17574207^Y
UNII	A9M89XG7QW
CompTox Dashboard (EPA)	DTXSID301032900
Chemical and physical data
Formula	C₁₁H₁₆BrNO₃
Molar mass	290.157 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=C(C(=C(C(=C1)CCN)Br)OC)OC
InChI InChI=1S/C11H16BrNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3 Key:UXQBKANLBLUVMK-UHFFFAOYSA-N

2-Bromomescaline

See also

References

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