Compound: Synephrine
SMILES: Oc1ccc(C(O)CNC)cc1
InChIKey: YRCWQPVGYLYSOX-UHFFFAOYSA-N
Synonyms: Synephrine, Oxedrine, 94-07-5, p-Synephrine, Parasympatol, Analeptin, Sympatol, Simpalon, Synthenate, Sympathol, Ethaphene, DL-SYNEPHRINE, 4-[1-Hydroxy-2-(methylamino)ethyl]phenol, 4-(1-Hydroxy-2-(methylamino)ethyl)phenol, Advantra z, 1-(4-Hydroxyphenyl)-2-methylaminoethanol, DTXSID0030588, NSC-166285, NSC-170956, PEG5DP7434, CHEBI:29081, beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcohol, 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol, Benzenemethanol, 4-hydroxy-alpha-((methylamino)methyl)-, 4-Hydroxy-alpha-((methylamino)methyl)benzenemethanol, p-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol, S-38537-9, DTXCID8010588, p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol, 4-hydroxy-alpha-[(methylamino)methyl]benzenemethanol, Benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-, (+-)-synephrine, RefChem:186991, 202-300-9, Sympaethamine, (+/-)-Synephrine, Sympaethamin, Synephrin, Simpatol, p-Oxedrine, Synefrin, MFCD00002370, rac-Synephrine, 1-(4-Hydroxyphenyl)-N-methylethanolamine, (RS)-1-(4-Hydroxyphenyl)-2-(methylamino)ethanol, NSC 166285, S 38537-9, Benzenemethanol, 4-hydroxy-a-[(methylamino)methyl]-, (aR)-, NSC166285, Benzenemethanol, 4-hydroxy-.alpha.-[(methylamino)methyl]-, 1-(4-Hydroxyphenyl)-(2-methylamino)ethanol, WLN: QR DYQ1M1, Synefrin [Czech], p-((Methylamino)ethanol)phenol, p-[(Methylamino)ethanol]phenol, p-Hydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol, Parakorper [German], .beta.-Methylamino-.alpha.-(4-hydroxyphenyl)ethyl alcohol, Benzyl alcohol, p-hydroxy-.alpha.-[(methylamino)methyl]-, Parakorper, p-Hydroxyphenyl(methylamino)ethanol, p-Methylaminoethanolphenol, benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-, 2,3-dihydroxybutanedioate (1:1) (salt), SMR000059111, SYNEPHERINE, 1-(4-Hydroxyphenyl)-(N-methylethanol)amine, p-Hydroxyphenylmethylaminoethanol, 1-(4-hydroxyphenyl)-2-(methylamino)ethan-1-ol, Oxedrine [INN:BAN], ((Methylamino)methyl)((4-hydroxyphenyl)carbinol), [(Methylamino)methyl][(4-hydroxyphenyl)carbinol], SR-01000002983, p-Hydroxy-.alpha.-[(methylamino)methyl]benzylalcohol, EINECS 202-300-9, (+-)-N-Methyloctopamine, benzene, 1-hydroxy-4-(1-hydroxy-2-methylamino)ethyl-, UNII-PEG5DP7434, Methylaminomethyl(4-hydroxyphenyl)carbinol, Analeptin;, BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, Ethaphene;, Oxedrine;, Simpalon;, (y)-Synephrine, (?-Synephrine, CAS-94-07-5, NCGC00016351-01, Oxedrine, Sympatol, (?)-Synephrine, Oxedrine (BAN), (+,-)-Synephrine, NSC 170956, Synephrine (Oxedrine), Synephrine (Standard), ( inverted exclamation markA)-Synephrine, alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan [German], Adrenaline Impurity 33, SYNEPHRINE [MI], Prestwick0_001088, Prestwick1_001088, Prestwick2_001088, Prestwick3_001088, (.+/-.)-Synephrine, OXEDRINE [MART.], OXEDRINE [WHO-DD], (+/-)-N-Methyloctopamine, SYNEPHRINE [USP-RS], 4-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol, Lopac0_001085, (+/-)-OXEDRINE, BSPBio_001136, alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan, MLS000069435, MLS001424216, CHEMBL33720, SCHEMBL146500, SPBio_003028, Synephrine, analytical standard, (.+/-.)-N-Methyloctopamine, BPBio1_001250, orb1309115, orb3140765, SCHEMBL5120171, OXEDRINE [USP IMPURITY], HY-N0132R, (+/-)-Synephrine, >=98%, BENZYL ALCOHOL, p-HYDROXY-alpha-((METHYLAMINO)METHYL)-, HMS1571I18, HMS2052G09, HMS2098I18, HMS2233F20, HMS3263I12, HMS3264E11, HMS3369C13, HMS3394G09, HMS3656O09, HMS3715I18, HMS3884D15, HMS5080J16, Pharmakon1600-01506085, ALBB-025740, HY-N0132, MSK40086, Tox21_110390, Tox21_200962, Tox21_501085, ( inverted question mark)-Synephrine, BBL015111, BDBM50102660, EBC-12197, NSC170956, NSC759316, PDSP1_000167, PDSP2_000166, s2362, SBB063601, STK803113, AKOS004119915, AKOS016038542, Tox21_110390_1, CCG-101098, CCG-205162, DB09203, KS-5152, LP01085, NC00348, NSC-759316, SDCCGSBI-0051055.P003, NCGC00015924-03, NCGC00015924-04, NCGC00015924-05, NCGC00015924-06, NCGC00015924-08, NCGC00015924-09, NCGC00015924-12, NCGC00015924-13, NCGC00015924-25, NCGC00089788-02, NCGC00089788-03, NCGC00089788-04, NCGC00258515-01, NCGC00261770-01, (+)-[(methylamino)methyl]-Benzenemethano, 4-(1-Hydroxy-2-methylamino-ethyl)phenol, BP-12742, FS157243, ST095769, SY078448, SBI-0051055.P002, AB00514040, CS-0007857, EU-0101085, NS00007649, S0232, SW197214-5, 4-[1-Hydroxy-2-(methylamino)ethyl]phenol #, 4-Hydroxy-a-(methylaminomethyl)benzyl alcohol, C04548, D07148, EN300-267997, S 0752, 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, AB00384265_11, Q421351, SR-01000002983-3, SR-01000002983-7, SR-01000002983-8, BRD-A04327189-001-14-4, BRD-A04327189-001-15-1, BRD-A04327189-001-16-9, BRD-A04327189-003-02-5, BRD-A04327189-003-03-3, 4-Hydroxy-.alpha.-((methylamino)methyl)benzenemethanol, 7336264B-EDC9-42C5-939B-FF800AB5BB4A
Theoretical properties:
molecular_formula: C9H13NO2
molecular_weight: 167.20 g/mol
exact_mass: 167.094628657 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 52.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Synephrine is a phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen. It has a role as an alpha-adrenergic agonist and a plant metabolite. It is a member of ethanolamines, a member of phenols and a phenethylamine alkaloid. It is a conjugate base of a synephrinium.", "chebi": "A  phenethylamine alkaloid that is 4-(2-aminoethyl)phenol substituted by a hydroxy group at position 1 and a methyl group at the amino nitrogen.", "chembl": "OXEDRINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.", "wikipedia": "Synephrine, or, more specifically, p-synephrine, is an alkaloid, occurring naturally in some plants and animals, and also in approved drugs products as its m-substituted analog known as neo-synephrine. p-Synephrine (or formerly Sympatol and oxedrine [BAN]) and m-synephrine are known for their longer acting adrenergic effects compared to epinephrine and norepinephrine. This substance is present at very low concentrations in common foodstuffs such as orange juice and other orange (Citrus species) products, both of the \"sweet\" and \"bitter\" variety. The preparations used in traditional Chinese medicine (TCM), also known as Zhi Shi (\u67b3\u5b9e), are the immature and dried whole oranges from Citrus aurantium (Fructus Aurantii Immaturus). Extracts of the same material or purified synephrine are also marketed in the US, sometimes in combination with caffeine, as a weight-loss-promoting dietary supplement for oral consumption. While the traditional preparations have been in use for millennia as a component of TCM-formulas, synephrine itself is not an approved over the counter drug. As a pharmaceutical, m-synephrine (phenylephrine) is still used as a sympathomimetic (i.e. for its hypertensive and vasoconstrictor properties), mostly by injection for the treatment of emergencies such as shock, and rarely orally for the treatment of bronchial problems associated with asthma and hay-fever.\nThere is a difference between studies concerning synephrine as a single chemical entity (synephrine can exist in the form of either of two stereoisomers, d- and l-synephrine, which are chemically and pharmacologically distinct), and synephrine which is mixed with other drugs and/or botanical extracts in a \"supplement\", as well as synephrine which is present as only one chemical component in a naturally-occurring mixture of phytochemicals such as the rind or fruit of a bitter orange. Mixtures containing synephrine as only one of their chemical components (regardless of whether these are of synthetic or natural origin) should not be assumed to produce exactly the same biological effects as synephrine alone.\nIn physical appearance, synephrine is a colorless, crystalline solid and is water-soluble. Its molecular structure is based on a phenethylamine skeleton and is related to those of many other drugs and to the major neurotransmitters epinephrine and norepinephrine."}