TCB-2

TCB-2
Systematic (IUPAC) name
	[(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Clinical data
Routes of; administration	Oral
Legal status
Legal status	Uncontrolled;
Identifiers
CAS Number	912440-88-1 ; 912342-36-0 (hydrobromide)
ATC code	none
PubChem	CID 16086382
ChemSpider	17245036
ChEMBL	CHEMBL379637
Chemical data
Formula	C11H14BrNO2
Molar mass	272.14 g/mol
	SMILES COc1c(Br)cc(OC)c2c1CC2CN ;
	InChI InChI=1S/C11H14BrNO2/c1-14-9-4-8(12)11(15-2)7-3-6(5-13)10(7)9/h4,6H,3,5,13H2,1-2H3/t6-/m0/s1 ; Key:MPBCKKVERDTCEL-LURJTMIESA-N ;
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TCB-2 is a hallucinogen, discovered in 2006 by Thomas McLean, working in the lab of Prof. David Nichols at Purdue University where it was named 2C-BCB.^[1] It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonist for the 5-HT_2A and 5-HT_2C receptors with a K_i of 0.26nM at the human 5-HT_2A receptor. In drug-substitution experiments in rats, TCB-2 was found to be of similar potency to both LSD and Br-DFLY, ranking it among the most potent phenethylamine hallucinogens yet discovered.^[2] This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT_2A mediated responses from those produced by other similar receptors.^[3] TCB-2 has similar but not identical effects in animals to related phenethylamine hallucinogens such as DOI, and has been used for studying how the function of the 5-HT_2A receptor differs from that of other serotonin receptors in a number of animal models, such as studies of cocaine addiction and neuropathic pain.^[4]^[5]^[6]^[7]

References[edit]

^ Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD (November 2008). "Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency". J. Pharmacol. Exp. Ther. 327 (2): 316–23. doi:10.1124/jpet.108.143461. PMID 18708586.
^ McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE. 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT_2A receptor agonists. Journal of Medicinal Chemistry. 2006 Sep 21;49(19):5794-803. PMID 16970404
^ Chang CW, Poteet E, Schetz JA, Gümüş ZH, Weinstein H. Towards a quantitative representation of the cell signaling mechanisms of hallucinogens: measurement and mathematical modeling of 5-HT_1A and 5-HT_2A receptor-mediated ERK1/2 activation. Neuropharmacology. 2009;56 Suppl 1:213-25. PMID 18762202
^ Fox, M. A.; French, H. T.; Laporte, J. L.; Blackler, A. R.; Murphy, D. L. (2009). "The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis". Psychopharmacology. 212 (1): 13–23. doi:10.1007/s00213-009-1694-1. PMID 19823806.
^ Aira, Z.; Buesa, I.; Salgueiro, M.; Bilbao, J.; Aguilera, L.; Zimmermann, M.; Azkue, J. J. (2010). "Subtype-specific changes in 5-HT receptor-mediated modulation of C fibre-evoked spinal field potentials are triggered by peripheral nerve injury". Neuroscience. 168 (3): 831–841. doi:10.1016/j.neuroscience.2010.04.032. PMID 20412834.
^ Katsidoni, V.; Apazoglou, K.; Panagis, G. (2010). "Role of serotonin 5-HT2A and 5-HT2C receptors on brain stimulation reward and the reward-facilitating effect of cocaine". Psychopharmacology. 213 (2–3): 337–354. doi:10.1007/s00213-010-1887-7. PMID 20577718.
^ Zhang, G.; Ásgeirsdóttir, H. N.; Cohen, S. J.; Munchow, A. H.; Barrera, M. P.; Stackman, R. W. (2012). "Stimulation of serotonin 2A receptors facilitates consolidation and extinction of fear memory in C57BL/6J mice". Neuropharmacology. 64: 403–13. doi:10.1016/j.neuropharm.2012.06.007. PMC 3477617. PMID 22722027.

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[1] Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD (November 2008). "Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency". J. Pharmacol. Exp. Ther. 327 (2): 316–23. doi:10.1124/jpet.108.143461. PMID 18708586.

[2] McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE. 1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT_2A receptor agonists. Journal of Medicinal Chemistry. 2006 Sep 21;49(19):5794-803. PMID 16970404

[3] Chang CW, Poteet E, Schetz JA, Gümüş ZH, Weinstein H. Towards a quantitative representation of the cell signaling mechanisms of hallucinogens: measurement and mathematical modeling of 5-HT_1A and 5-HT_2A receptor-mediated ERK1/2 activation. Neuropharmacology. 2009;56 Suppl 1:213-25. PMID 18762202

[4] Fox, M. A.; French, H. T.; Laporte, J. L.; Blackler, A. R.; Murphy, D. L. (2009). "The serotonin 5-HT2A receptor agonist TCB-2: A behavioral and neurophysiological analysis". Psychopharmacology. 212 (1): 13–23. doi:10.1007/s00213-009-1694-1. PMID 19823806.

[5] Aira, Z.; Buesa, I.; Salgueiro, M.; Bilbao, J.; Aguilera, L.; Zimmermann, M.; Azkue, J. J. (2010). "Subtype-specific changes in 5-HT receptor-mediated modulation of C fibre-evoked spinal field potentials are triggered by peripheral nerve injury". Neuroscience. 168 (3): 831–841. doi:10.1016/j.neuroscience.2010.04.032. PMID 20412834.

[6] Katsidoni, V.; Apazoglou, K.; Panagis, G. (2010). "Role of serotonin 5-HT2A and 5-HT2C receptors on brain stimulation reward and the reward-facilitating effect of cocaine". Psychopharmacology. 213 (2–3): 337–354. doi:10.1007/s00213-010-1887-7. PMID 20577718.

[7] Zhang, G.; Ásgeirsdóttir, H. N.; Cohen, S. J.; Munchow, A. H.; Barrera, M. P.; Stackman, R. W. (2012). "Stimulation of serotonin 2A receptors facilitates consolidation and extinction of fear memory in C57BL/6J mice". Neuropharmacology. 64: 403–13. doi:10.1016/j.neuropharm.2012.06.007. PMC 3477617. PMID 22722027.

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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-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA

Amphetamines	Psychedelics: 3C-BZ 3C-E 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 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamine 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 Phenpromethamine 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 MDEA MDHMA MDMA MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DFMDA 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 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) Theodrenaline Thiamphenicol UWA-101

TCB-2

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Systematic (IUPAC) name

[(7R)-3-Bromo-2,5-dimethoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl]methanamine
Clinical data
Routes of administration	Oral
Legal status
Legal status	Uncontrolled
Identifiers
CAS Number	912440-88-1^Y 912342-36-0 (hydrobromide)
ATC code	none
PubChem	CID 16086382
ChemSpider	17245036
ChEMBL	CHEMBL379637
Chemical data
Formula	C₁₁H₁₄BrNO₂
Molar mass	272.14 g/mol
SMILES COc1c(Br)cc(OC)c2c1CC2CN
InChI InChI=1S/C11H14BrNO2/c1-14-9-4-8(12)11(15-2)7-3-6(5-13)10(7)9/h4,6H,3,5,13H2,1-2H3/t6-/m0/s1 Key:MPBCKKVERDTCEL-LURJTMIESA-N
(verify)