Metanephrine

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Metanephrine
Names

IUPAC name 4-(1-hydroxy-2-methylamino-ethyl)-2-methoxy-phenol
Identifiers
CAS Number	5001-33-2^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL775^Y
ChemSpider	19844^Y
IUPHAR/BPS	6644
MeSH	Metanephrine
PubChem CID	21100
UNII	1ZE0530JEJ^Y
CompTox Dashboard (EPA)	DTXSID80863478
InChI InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3^Y Key: JWJCTZKFYGDABJ-UHFFFAOYSA-N^Y InChI=1/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3 Key: JWJCTZKFYGDABJ-UHFFFAOYAB
SMILES Oc1ccc(cc1OC)C(O)CNC
Properties
Chemical formula	C₁₀H₁₅NO₃
Molar mass	197.231 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Metanephrine, also known as metadrenaline, is a metabolite of epinephrine (also known as adrenaline) created by action of catechol-O-methyl transferase on epinephrine. An article in the Journal of the American Medical Association, 2002, indicated that the measurement of plasma free levels of the metanephrines group of molecules (including metanephrine and normetanephrine) is the best tool in the diagnosis of pheochromocytoma, an adrenal medullary neoplasm.^[1]

epinephrine

References

[edit]

^ Lenders J, Pacak K, Walther M, Linehan W, Mannelli M, Friberg P, Keiser H, Goldstein D, Eisenhofer G (2002). "Biochemical diagnosis of pheochromocytoma: which test is best?". JAMA. 287 (11): 1427–34. doi:10.1001/jama.287.11.1427. PMID 11903030. Free full text with registration

Neurotransmitter metabolic intermediates

Catecholamines

Anabolism

Phenylalanine → Tyrosine → DOPA (levodopa) → Dopamine → Norepinephrine → Epinephrine

Catabolism

Dopamine	3,4-Dihydroxyphenylacetaldehyde (DOPAL) 3,4-Dihydroxyphenylacetic acid (DOPAC) Homovanillyl alcohol Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET) 3-Methoxytyramine (3-MT) Homovanillic acid (HVA)
Norepinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) 3,4-Dihydroxymandelic acid (DHMA) Normetanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL) Vanillylmandelic acid (VMA) 3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG) 3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
Epinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) Metanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL)

Tryptophan→Serotonin

Anabolism	Tryptophan 5-Hydroxytryptophan (5-HTP)
Catabolism	5-Hydroxyindoleacetaldehyde (5-HIAL) 5-Hydroxyindoleacetic acid (5-HIAA) 5-Hydroxytryptophol (5-HTOL)

Entactogens: Lophophine
MDPEA
MDMPEA

Amphetamines

Stimulants: 2-FA
2-FMA
3-FA
3-FMA
β-Phenylmethamphetamine
Acridorex
Alfetamine
Amfecloral
Amfepentorex
Amphetamine
- Dextroamphetamine
- Levoamphetamine
Amphetaminil
Benfluorex
Benzphetamine
Cathine
Clobenzorex
Dimethylamphetamine
Ephedrine
Ephenidine
Etafedrine
Etilamfetamine
Famprofazone
Fencamfamin
Fencamine
Fenethylline
Fenfluramine
- Dexfenfluramine
- Levofenfluramine
Fenproporex
Flucetorex
Fludorex
Formetorex
Furfenorex
Gepefrine
4-Hydroxyamphetamine
Iofetamine
Isopropylamphetamine
Lefetamine
Lisdexamfetamine
Mefenorex
Metaraminol
Methamphetamine
- Dextromethamphetamine
- Levomethamphetamine
Methoxamine
Methoxyphenamine
MMA
Morforex
Norfenfluramine
L-Norpseudoephedrine
α,N-Diethylphenylethylamine
Oxifentorex
Oxilofrine
Ortetamine
PBA
PBMA
PCA
PCMA
PFA
PFMA
PIA
PIMA
PMA
PMEA
PMMA
Phenylpropanolamine
Pholedrine
Prenylamine
Propylamphetamine
Pseudoephedrine
Sibutramine
Tiflorex
Xylopropamine
Zylofuramine

Others: 3,4-DCA
Amiflamine
Cafedrine
Deprenyl
- D-Deprenyl
- Selegiline (L-deprenyl)
DiFMDA
Thiamphenicol
UWA-101 (α-cPr-MDMA)

Phentermines

Entactogens: MDPH
MDMPH

Others: Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants: α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Calycotomine Debrisoquine Deutetrabenazine Diclofensine Esproquin Gigantine Hedycarine Lophophorine Lophotine Nomifensine Norsalsolinol Pellotine Perafensine Peyophorine Peyotine Quinisocaine Reticuline Salsoline Salsolinol Tetrabenazine Tetrahydroisoquinoline Tetrahydropapaveroline Tilisolol Tretoquinol Valbenazine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indanorex Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 DOM-AT MDAT MDMAT UH-232
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) Benzocyclobutenes (e.g., 2CBCB-NBOMe, S33005, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) 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

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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