Chemistry:2C-B-morpholine

2C-B-morpholine, also known as 2C-B-norphenmetrazine or as 2-(4-bromo-2,5-dimethoxyphenyl)morpholine, is a serotonin receptor modulator of the phenylmorpholine (phenmetrazine) and cyclized phenethylamine groups.^[1] It is a ligand of the serotonin 5-HT_2A receptor, with an affinity of 20.6 nM and an E_max of 4%.^[1] The drug showed 103-fold lower affinity for this receptor than R(–)-DOB and had minimal agonist activity (with R(–)-DOB having an E_max of 51% in the assay), so for practical purposes would act as an antagonist at the 5-HT_2A receptor under most circumstances, despite being technically classified as a partial agonist.^[1] 2C-B-morpholine was first described in the scientific literature by Richard Glennon and colleagues by 2004.^[1]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry 47 (24): 6034–6041. November 2004. doi:10.1021/jm040082s. PMID 15537358. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=db12f5229bdabb798f5f0682120f9c7c5d20f479. "One of the first compounds prepared and examined in this investigation was morpholine analogue 2. Compound 2 bears an ether oxygen atom at the benzylic position that is tethered to the terminal amine. However, its 5-HT2A affinity (Ki) 20.6 nM) is 100-fold lower than that of R(-)DOB (Ki) 0.2 nM), and its agonist efficacy in the 5-HT2-mediated calcium mobilization assay is minimal (Table 1). There are several possible explanations for these unfavorable findings. Apart from the molecule possessing a chiral center, the ether oxygen atom might not be tolerated by the receptor and/or the added ethylene “bridge” might not be readily accommodated by the receptor and its presence detracts from affinity. A more plausible explanation, based on prior structure-affinity investigations, is that the secondary amine of 2 contributes to decreased affinity. That is, we have previously shown that addition of small N-alkyl substituents can reduce the 5-HT2A receptor affinity of DOB and DOB-related compounds.16,17".

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[Glennon_2004-1] 1.0 ^1.1 ^1.2 ^1.3 "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry 47 (24): 6034–6041. November 2004. doi:10.1021/jm040082s. PMID 15537358. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=db12f5229bdabb798f5f0682120f9c7c5d20f479. "One of the first compounds prepared and examined in this investigation was morpholine analogue 2. Compound 2 bears an ether oxygen atom at the benzylic position that is tethered to the terminal amine. However, its 5-HT2A affinity (Ki) 20.6 nM) is 100-fold lower than that of R(-)DOB (Ki) 0.2 nM), and its agonist efficacy in the 5-HT2-mediated calcium mobilization assay is minimal (Table 1). There are several possible explanations for these unfavorable findings. Apart from the molecule possessing a chiral center, the ether oxygen atom might not be tolerated by the receptor and/or the added ethylene “bridge” might not be readily accommodated by the receptor and its presence detracts from affinity. A more plausible explanation, based on prior structure-affinity investigations, is that the secondary amine of 2 contributes to decreased affinity. That is, we have previously shown that addition of small N-alkyl substituents can reduce the 5-HT2A receptor affinity of DOB and DOB-related compounds.16,17".

[1]

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 α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate 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 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 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 (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
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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

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