Metaraminol

Metaraminol

Systematic (IUPAC) name
(1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	C(AU) C(US)
Legal status	POM (UK)
Routes	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Protein binding	~45%
Metabolism	Hepatic
Identifiers
CAS number	54-49-9^Y
ATC code	C01CA09
PubChem	CID 5906
DrugBank	APRD00555
ChemSpider	5695^Y
UNII	818U2PZ2EH^Y
KEGG	D08192^Y
ChEBI	CHEBI:6794^Y
ChEMBL	CHEMBL1201319^N
Chemical data
Formula	C₉H₁₃N O₂
Mol. mass	167.205 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1^Y Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N^Y
N(what is this?) (verify)

Metaraminol (INN, trade name Aramine) is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is an α₁-adrenergic receptor agonist with some β effect.

Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.^[1]^[2]^[3]

Chemistry

Metaraminol, L-1-(3-hydroxyphenyl)-2-aminopropan-1-ol, is synthesized in two ways. The first way is synthetic, and it is from 3-hydroxypropiophenone. The hydroxyl group is protected by alkylation with benzyl chloride, giving 3-benzyloxypropiophenone. Upon reaction with butyl nitrite, it undergoes nitrosation into the isonitrosoketone, which by reduction using hydrogen over Raney nickel turns into 1-(3-benzyloxyphenyl)-2-aminopropan-1-ol, the protecting benzyl group is removed by reduction using hydrogen over palladium catalyst, to give racemic metaraminol. The desired L-isomer is isolated with the help of (+)-tartaric acid.

G. Erhart, L. Stein, DE 555404 (1930).
E. W. Zeh, U.S. Patent 1,951,229 (1934).

The second way is semisynthetic, consisting of fermentation of D-glucose in the presence of 3-acetoxybenzaldehyde, which forms (-)-1-hydroxy-1-(3-hydroxyphenyl)-acetone, the carbonyl group of which is reduced by hydrogen over a palladium catalyst in the presence of ammonia, giving metaraminol.

G. Erhart, L. Stein, DE 571229 (1930).
G. Erhart, L. Stein, U.S. Patent 1,948,162 (1934).
W. H. Hartung, U.S. Patent 1,995,709 (1935).
I. G. Farbenindustrie AG, GB 396951 (1932).

References

^ McDonald M, Santucci R (2004). "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.". Int Braz J Urol 30 (2): 121–2. doi:10.1590/S1677-55382004000200007. PMID 15703094.
^ Koga S, Shiraishi K, Saito Y (1990). "Post-traumatic priapism treated with metaraminol bitartrate: case report.". J Trauma 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). "[Metaraminol in therapy of various forms of priapism]". Urologe A 27 (4): 225–9. PMID 3140463.

Adrenergics

Receptor ligands

α₁	Agonists: 5-FNE • 6-FNE • Amidephrine • Anisodamine • Anisodine • Cirazoline • Dipivefrine • Dopamine • Ephedrine • Epinephrine (Adrenaline) • Etilefrine • Ethylnorepinephrine • Indanidine • Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Midodrine • Naphazoline • Norepinephrine (Noradrenaline) • Octopamine • Oxymetazoline • Phenylephrine • Phenylpropanolamine • Pseudoephedrine • Synephrine • Tetrahydrozoline Antagonists: Abanoquil • Adimolol • Ajmalicine • Alfuzosin • Amosulalol • Arotinolol • Atiprosin • Benoxathian • Buflomedil • Bunazosin • Carvedilol • CI-926 • Corynanthine • Dapiprazole • DL-017 • Domesticine • Doxazosin • Eugenodilol • Fenspiride • GYKI-12,743 • GYKI-16,084 • Indoramin • Ketanserin • L-765,314 • Labetalol • Mephendioxan • Metazosin • Monatepil • Moxisylyte (Thymoxamine) • Naftopidil • Nantenine • Neldazosin • Nicergoline • Niguldipine • Pelanserin • Phendioxan • Phenoxybenzamine • Phentolamine • Piperoxan • Prazosin • Quinazosin • Ritanserin • RS-97,078 • SGB-1,534 • Silodosin • SL-89.0591 • Spiperone • Talipexole • Tamsulosin • Terazosin • Tibalosin • Tiodazosin • Tipentosin • Tolazoline • Trimazosin • Upidosin • Urapidil • Zolertine * Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone, trazodone, nefazodone, etoperidone, and mepiprazole all antagonize α₁-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.

α₂	Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • 6-FNE • Amitraz • Apraclonidine • Brimonidine • Cannabivarin • Clonidine • Detomidine • Dexmedetomidine • Dihydroergotamine • Dipivefrine • Dopamine • Ephedrine • Ergotamine • Epinephrine (Adrenaline) • Esproquin • Etilefrine • Ethylnorepinephrine • Guanabenz • Guanfacine • Guanoxabenz • Levonordefrin • Lofexidine • Medetomidine • Methyldopa • Mivazerol • Naphazoline • Norepinephrine (Noradrenaline) • Phenylpropanolamine • Piperoxan • Pseudoephedrine • Rilmenidine • Romifidine • Talipexole • Tetrahydrozoline • Tizanidine • Tolonidine • Urapidil • Xylazine • Xylometazoline Antagonists: 1-PP • Adimolol • Aptazapine • Atipamezole • BRL-44408 • Buflomedil • Cirazoline • Efaroxan • Esmirtazapine • Fenmetozole • Fluparoxan • GYKI-12,743 • GYKI-16,084 • Idazoxan • Mianserin • Mirtazapine • MK-912 • NAN-190 • Olanzapine • Phentolamine • Phenoxybenzamine • Piperoxan • Piribedil • Rauwolscine • Rotigotine • SB-269,970 • Setiptiline • Spiroxatrine • Sunepitron • Tolazoline • Yohimbine * Note that many atypical antipsychotics and azapirones like buspirone and gepirone (via metabolite 1-PP) antagonize α₂-adrenergic receptors as well.

β	Agonists: 2-FNE • 5-FNE • Amibegron • Arbutamine • Arformoterol • Arotinolol • BAAM • Bambuterol • Befunolol • Bitolterol • Broxaterol • Buphenine • Carbuterol • Cimaterol • Clenbuterol • Denopamine • Deterenol • Dipivefrine • Dobutamine • Dopamine • Dopexamine • Ephedrine • Epinephrine (Adrenaline) • Etafedrine • Etilefrine • Ethylnorepinephrine • Fenoterol • Formoterol • Hexoprenaline • Higenamine • Indacaterol • Isoetarine • Isoprenaline (Isoproterenol) • Isoxsuprine • Labetalol • Levonordefrin • Levosalbutamol • Mabuterol • Methoxyphenamine • Methyldopa • N-Isopropyloctopamine • Norepinephrine (Noradrenaline) • Orciprenaline • Oxyfedrine • Phenylpropanolamine • Pirbuterol • Prenalterol • Ractopamine • Procaterol • Pseudoephedrine • Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Solabegron • Terbutaline • Tretoquinol • Tulobuterol • Xamoterol • Zilpaterol • Zinterol Antagonists: Acebutolol • Adaprolol • Adimolol • Afurolol • Alprenolol • Alprenoxime • Amosulalol • Ancarolol • Arnolol • Arotinolol • Atenolol • Befunolol • Betaxolol • Bevantolol • Bisoprolol • Bopindolol • Bormetolol • Bornaprolol • Brefonalol • Bucindolol • Bucumolol • Bufetolol • Buftiralol • Bufuralol • Bunitrolol • Bunolol • Bupranolol • Burocrolol • Butaxamine • Butidrine • Butofilolol • Capsinolol • Carazolol • Carpindolol • Carteolol • Carvedilol • Celiprolol • Cetamolol • Cicloprolol • Cinamolol • Cloranolol • Cyanopindolol • Dalbraminol • Dexpropranolol • Diacetolol • Dichloroisoprenaline • Dihydroalprenolol • Dilevalol • Diprafenone • Draquinolol • Dropranolol • Ecastolol • Epanolol • Ericolol • Ersentilide • Esatenolol • Esmolol • Esprolol • Eugenodilol • Exaprolol • Falintolol • Flestolol • Flusoxolol • Hydroxycarteolol • Hydroxytertatolol • ICI-118,551 • Idropranolol • Indenolol • Indopanolol • Iodocyanopindolol • Iprocrolol • Isoxaprolol • Isamoltane • Labetalol • Landiolol • Levobetaxolol • Levobunolol • Levocicloprolol • Levomoprolol • Medroxalol • Mepindolol • Metalol • Metipranolol • Metoprolol • Moprolol • Nadolol • Nadoxolol • Nafetolol • Nebivolol • Neraminol • Nifenalol • Nipradilol • Oberadilol • Oxprenolol • Pacrinolol • Pafenolol • Pamatolol • Pargolol • Parodilol • Penbutolol • Penirolol • PhQA-33 • Pindolol • Pirepolol • Practolol • Primidolol • Procinolol • Pronethalol • Propafenone • Propranolol • Ridazolol • Ronactolol • Soquinolol • Sotalol • Spirendolol • SR 59230A • Sulfinalol • TA-2005 • Talinolol • Tazolol • Teoprolol • Tertatolol • Terthianolol • Tienoxolol • Tilisolol • Timolol • Tiprenolol • Tolamolol • Toliprolol • Tribendilol • Trigevolol • Xibenolol • Xipranolol

Reuptake inhibitors

NET	Selective norepinephrine reuptake inhibitors: Amedalin • Atomoxetine (Tomoxetine) • Ciclazindol • Daledalin • Esreboxetine • Lortalamine • Mazindol • Nisoxetine • Reboxetine • Talopram • Talsupram • Tandamine • Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • Levophacetoperane • LR-5182 • Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Eclanamine • Levomilnacipran • Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • JNJ-7925476 • JZ-IV-10 • Methylnaphthidate • Naphyrone • NS-2359 • PRC200-SS • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • melitracen • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline • Setiptiline; Others: Cocaine • CP-39,332 • EXP-561 • Fezolamine • Ginkgo biloba • Indeloxazine • Nefazodone • Nefopam • Pridefrine • Tapentadol • Tedatioxetine • Teniloxazine • Tramadol • Ziprasidone

VMAT	Ibogaine • Reserpine • Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-OH-PEA • 4-CAB • 4-FA • 4-FMA • 4-MA • 4-MMA • Alfetamine • Amfecloral • Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Me-PEA • BDB • Benzphetamine • BOH • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • DMA • DMMA • EBDB • Ephedrine • Ethcathinone • Ethylamphetamine • Ethylone • Famprofazone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • IAP • IMP • L-Deprenyl (Selegiline) • Lisdexamfetamine • Lophophine • MBDB • MDA (Tenamfetamine) • MDEA • MDMA • MDMPEA • MDOH • MDPEA • Mefenorex • Mephedrone • Mephentermine • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methcathinone • Methedrone • Methylone • NAP • Ortetamine • Paredrine • pBA • pCA • Pentorex (Phenpentermine) • Phenethylamine • Pholedrine • Phenpromethamine • Phentermine • Phenylpropanolamine • pIA • Prenylamine • Propylamphetamine • Pseudoephedrine • Tiflorex • Tyramine • Xylopropamine • Zylofuramine; Piperazines: 2C-B-BZP • BZP • MBZP • mCPP • MDBZP • MeOPP • pFPP; Others: 2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-Benzylpiperidine • 4-Benzylpiperidine • 5-IAI • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanorex • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine (Levopropylhexedrine) • Tuaminoheptane

Enzyme inhibitors

Anabolism

PAH	3,4-Dihydroxystyrene

TH	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD	Benserazide • Carbidopa • Genistein • Methyldopa

DBH	Bupicomide • Disulfiram • Dopastin • Fusaric acid • Nepicastat • Phenopicolinic acid • Tropolone

PNMT	CGS-19281A • SKF-64139 • SKF-7698

Catabolism

MAO	Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A selective: Amiflamine • Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone • Tyrima; MAO-B selective: D-Deprenyl • Selegiline (L-Deprenyl) • Ladostigil • Lazabemide • Milacemide • Mofegiline • Pargyline • Rasagiline • Safinamide * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT	Entacapone • Tolcapone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine • L-DOPS (Droxidopa)

Cofactors	Ferrous Iron (Fe²⁺) • S-Adenosyl-L-Methionine • Vitamin B₃ (Niacin, Nicotinamide → NADPH) • Vitamin B₆ (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B₉ (Folic acid → Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn²⁺)

Others	Activity enhancers: BPAP • PPAP; Release blockers: Bethanidine • Bretylium • Guanadrel • Guanazodine • Guanclofine • Guanethidine • Guanoxan; Toxins: Oxidopamine (6-Hydroxydopamine)

List of adrenergic drugs

Phenethylamines

Phenethylamines	Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 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-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: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA) Entactogens: Lophophine • MDPEA • MDMPEA Others: BOH • DMPEA

Amphetamines Phenylisopropylamines	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: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)

Phentermines	Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine Entactogens: MDPH • MDMPH

Cathinones	Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone Entactogens: Ethylone • Methylone

Phenylisobutylamines	Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J) Stimulants: Phenylisobutylamine

Phenylalkylpyrrolidines	Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone

Catecholamines (and relatives..)	6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine

Miscellaneous	Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol

Metaraminol

Chemistry

See also

References