Norbudrine

Norbudrine
Clinical data
Other names	Norbutrine; RD-9338; N-Cyclobutylnoradrenaline; N-Cyclobutylnorepinephrine
Drug class	Sympathomimetic; Bronchodilator
Identifiers
	IUPAC name 4-[2-(cyclobutylamino)-1-hydroxyethyl]benzene-1,2-diol;
CAS Number	15686-81-4 ; 13329-35-6 (hydrochloride);
PubChem CID	166575;
ChemSpider	145768;
UNII	8P6T83567P;
ChEMBL	ChEMBL2106796;
CompTox Dashboard (EPA)	DTXSID50864619 ;
Chemical and physical data
Formula	C12H17NO3
Molar mass	223.272 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(C1)NCC(C2=CC(=C(C=C2)O)O)O;
	InChI InChI=1S/C12H17NO3/c14-10-5-4-8(6-11(10)15)12(16)7-13-9-2-1-3-9/h4-6,9,12-16H,1-3,7H2; Key:OVTZNVCECJYMDW-UHFFFAOYSA-N;

Norbudrine (INNTooltip International Nonproprietary Name; developmental code name RD-9338), also known as norbutrine (BANTooltip British Approved Name) or as N-cyclobutylnoradrenaline, is a drug of the phenethylamine and catecholamine families described as a sympathomimetic and bronchodilator which was never marketed.^[1]^[2]^[3] It is the N-cyclobutyl analogue of norepinephrine (noradrenaline).^[1]^[4] The drug was first described in the literature by 1966.^[1]

References

^ ^a ^b ^c Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1-PA215. ISBN 978-1-4757-2085-3. Retrieved 17 October 2024.
^ List PH, Hörhammer L (2013). Chemikalien und Drogen Teil A: N-Q. Handbuch der Pharmazeutischen Praxis - Vollständige (4.) Neuausgabe (in German). Springer Berlin Heidelberg. pp. 265–266. ISBN 978-3-642-65035-2. Retrieved 17 October 2024.
^ "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.
^ "Norbudrine". PubChem. U.S. National Library of Medicine. Retrieved 17 October 2024.

[Elks2014-1] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1-PA215. ISBN 978-1-4757-2085-3. Retrieved 17 October 2024.

[ListHörhammer2013-2] List PH, Hörhammer L (2013). Chemikalien und Drogen Teil A: N-Q. Handbuch der Pharmazeutischen Praxis - Vollständige (4.) Neuausgabe (in German). Springer Berlin Heidelberg. pp. 265–266. ISBN 978-3-642-65035-2. Retrieved 17 October 2024.

[WHO-INN-2018-3] "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.

[PubChem-4] "Norbudrine". PubChem. U.S. National Library of Medicine. Retrieved 17 October 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