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Chemical compound
Pharmaceutical compound
Meta-Hydroxynorephedrine |
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Other names | m-hydroxypropadrine m-hydroxyphenylpropanolamine α-methyl-m-octopamine 3,β-dihydroxyamphetamine 3,β-dihydroxy-α-methylphenethylamine |
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ATC code | |
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Legal status |
- In general: non-regulated
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3-(2-amino-1-hydroxypropyl)phenol
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CAS Number | |
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PubChem CID | |
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ChemSpider | |
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CompTox Dashboard (EPA) | |
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Formula | C9H13NO2 |
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Molar mass | 167.208 g·mol−1 |
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3D model (JSmol) | |
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InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3 Key:WXFIGDLSSYIKKV-UHFFFAOYSA-N
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meta-Hydroxynorephedrine or 3-hydroxynorephedrine, also known as 3,β-dihydroxyamphetamine, is an adrenergic drug of the amphetamine class which was patented as a vasopressor and nasal decongestant but was never marketed.[1][2] It is the racemic form of the sympathomimetic drug metaraminol.
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α1 | Agonists | |
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Antagonists |
- Abanoquil
- Ajmalicine
- Alfuzosin
- Anisodamine
- Anisodine
- Atiprosin
- Atypical antipsychotics (e.g., brexpiprazole, clozapine, olanzapine, quetiapine, risperidone)
- Benoxathian
- Beta blockers (e.g., adimolol, amosulalol, arotinolol, carvedilol, eugenodilol, labetalol)
- Buflomedil
- Bunazosin
- Corynanthine
- Dapiprazole
- Domesticine
- Doxazosin
- Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline, terguride)
- Etoperidone
- Fenspiride
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- mCPP
- Mepiprazole
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Niaprazine
- Niguldipine
- Pardoprunox
- Pelanserin
- Perlapine
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
- Piperoxan
- Prazosin
- Quinazosin
- Quinidine
- Silodosin
- Spegatrine
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tiodazosin
- Tolazoline
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin)
- Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine)
- Trimazosin
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Urapidil
- WB-4101
- Zolertine
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α2 | Agonists | |
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Antagonists |
- 1-PP
- Adimolol
- Amesergide
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, olanzapine, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, gepirone, ipsapirone, tandospirone)
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- Idazoxan
- Ketanserin
- Lisuride
- mCPP
- Mianserin
- Mirtazapine
- NAN-190
- Pardoprunox
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- Setiptiline
- Spegatrine
- Spiroxatrine
- Sunepitron
- Terguride
- Tolazoline
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Yohimbine
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β | |
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Phenethylamines | |
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Amphetamines | |
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Phentermines | |
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Cathinones | |
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Phenylisobutylamines (and further-extended) | |
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Catecholamines (and close relatives) | |
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Cyclized phenethylamines | Phenylalkylpyrrolidines | |
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2-Benzylpiperidines (phenidates) | |
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Phenylmorpholines (phenmetrazines) | |
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Phenyloxazolamines (aminorexes) | |
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Isoquinolines and tetrahydroisoquinolines | |
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2-Aminoindanes | |
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2-Aminotetralins | |
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Others / unsorted |
- 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, jimscaline)
- 2-ADN
- 2-Benzhydrylpyrrolidine
- 3-Benzhydrylmorpholine
- 3-Phenylpiperidines (e.g., 3-phenylpiperidine, OSU-6162 (PNU-96391), LPH-5, LPH-48)
- 6-AB
- AL-1095
- Benzazepines (e.g., fenoldopam, lorcaserin, SCHEMBL5334361)
- Bicyclo(4.2.0)octa-1,3,5-trienes (e.g., 2CBCB-NBOMe, S33005, TCB-2, tomscaline)
- Butyltolylquinuclidine
- Cypenamine (trans-2-phenylcyclopentylamine)
- Diphenidine
- Diphenylprolinol
- DMBMPP
- Ergolines (e.g., LSD)
- GYKI-52895
- HDMP-29
- Ivabradine
- Lumateperone and analogues (e.g., IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
- Methoxphenidine
- Methylmorphenate
- Milnacipran
- MT-45
- 2-Naphthylamine
- Org 6582
- Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, RU-27251)
- PF-592,379
- Phenylcyclopropylamines (e.g., DMCPA, TMT, Tranylcypromine)
- Tricyclics (e.g., benzoctamine, dizocilpine)
- Z3517967757
- ZC-B
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Related compounds |
- 2-Furylethylamine
- 2-Pyrrolylethylamine
- 3-Pyrrolylethylamine
- 3-Pyrrolylpropylamine
- 2-Tetrahydrofurylethylamine
- 4-Benzylpiperidine
- 7-AB
- Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
- Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
- Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
- Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
- Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
- Phenylalkenylamines (e.g., phenylbutenamine)
- Phenylalkynylamines (e.g., phenylbutynamine)
- Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
- Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
- Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)
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