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Synephrine

PubChem CID: 7172

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Compound Synonyms Synephrine, Oxedrine, 94-07-5, p-Synephrine, Parasympatol, Sympatol, Sympaethamine, (+/-)-Synephrine, Sympaethamin, Analeptin, Synephrin, Synthenate, Simpalon, Simpatol, Ethaphene, Sympathol, 4-[1-Hydroxy-2-(methylamino)ethyl]phenol, DL-SYNEPHRINE, p-Oxedrine, 4-(1-Hydroxy-2-(methylamino)ethyl)phenol, Parakorper [German], Parakorper, Synefrin, Advantra z, p-Methylaminoethanolphenol, 1-(4-Hydroxyphenyl)-2-methylaminoethanol, Oxedrine [INN:BAN], p-Hydroxyphenylmethylaminoethanol, rac-Synephrine, CHEBI:29081, 1-(4-Hydroxyphenyl)-N-methylethanolamine, (+-)-N-Methyloctopamine, (RS)-1-(4-Hydroxyphenyl)-2-(methylamino)ethanol, EINECS 202-300-9, UNII-PEG5DP7434, Oxedrine (BAN), NSC 166285, NSC-166285, NSC-170956, DTXSID0030588, Methylaminomethyl(4-hydroxyphenyl)carbinol, beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcohol, S 38537-9, 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol, SYNEPHRINE [MI], Benzenemethanol, 4-hydroxy-a-[(methylamino)methyl]-, (aR)-, OXEDRINE [MART.], OXEDRINE [WHO-DD], NSC 170956, 4-Hydroxy-alpha-((methylamino)methyl)benzenemethanol, SYNEPHRINE [USP-RS], (+/-)-OXEDRINE, (.+/-.)-N-Methyloctopamine, p-((Methylamino)ethanol)phenol, PEG5DP7434, OXEDRINE [USP IMPURITY], 1-(4-Hydroxyphenyl)-(2-methylamino)ethanol, DTXCID8010588, alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan [German], alpha-(4-Oxyphenyl)alpha-oxy-beta-methylaminoaethan, p-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol, 4-hydroxy-alpha-[(methylamino)methyl]benzenemethanol, NSC166285, S-38537-9, .beta.-Methylamino-.alpha.-(4-hydroxyphenyl)ethyl alcohol, Benzenemethanol, 4-hydroxy-.alpha.-[(methylamino)methyl]-, (+)-[(methylamino)methyl]-Benzenemethano, OXEDRINE (MART.), WLN: QR DYQ1M1, Synefrin [Czech], SYNEPHRINE (USP-RS), ((Methylamino)methyl)((4-hydroxyphenyl)carbinol), p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol, p-[(Methylamino)ethanol]phenol, 4-Hydroxy-.alpha.-((methylamino)methyl)benzenemethanol, p-Hydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol, OXEDRINE (USP IMPURITY), Benzyl alcohol, p-hydroxy-.alpha.-[(methylamino)methyl]-, p-Hydroxyphenyl(methylamino)ethanol, MFCD00002370, (+)-((Methylamino)methyl)-benzenemethano, SMR000059111, SYNEPHERINE, 1-(4-Hydroxyphenyl)-(N-methylethanol)amine, p-Hydroxy-a-((methylamino)methyl)benzyl alcohol, p-Hydroxy-a-[(methylamino)methyl]benzyl alcohol, 4-Hydroxy-a-((methylamino)methyl)benzenemethanol, 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, 4-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol, [(Methylamino)methyl][(4-hydroxyphenyl)carbinol], p-Hydroxy-I+--((methylamino)methyl)benzyl alcohol, p-Hydroxy-I+--[(methylamino)methyl]benzyl alcohol, SR-01000002983, 4-Hydroxy-I+--((methylamino)methyl)benzenemethanol, 4-Hydroxy-I+--[(methylamino)methyl]benzenemethanol, p-Hydroxy-.alpha.-[(methylamino)methyl]benzylalcohol, benzene, 1-hydroxy-4-(1-hydroxy-2-methylamino)ethyl-, Benzenemethanol, 4-hydroxy-alpha-((methylamino)methyl)-, -Synephrine, BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (y)-Synephrine, Synephrine,(S), CAS-94-07-5, NCGC00016351-01, Oxedrine, Sympatol, (?)-Synephrine, (+-)-synephrine, (+,-)-Synephrine, Synephrine (Oxedrine), Synephrine (Standard), ( inverted exclamation markA)-Synephrine, Prestwick0_001088, Prestwick1_001088, Prestwick2_001088, Prestwick3_001088, (.+/-.)-Synephrine, SYNEPHRINE [INCI], (+/-)-N-Methyloctopamine, Lopac0_001085, BSPBio_001136, MLS000069435, MLS001424216, CHEMBL33720, SCHEMBL146500, SPBio_003028, Synephrine, analytical standard, BPBio1_001250, HY-N0132R, (+/-)-Synephrine, >=98%, BENZYL ALCOHOL, p-HYDROXY-alpha-((METHYLAMINO)METHYL)-, HMS1571I18, HMS2052G09, HMS2098I18, HMS2233F20, HMS3263I12, HMS3264E11, HMS3369C13, HMS3394G09, HMS3656O09, HMS3715I18, HMS3884D15, Pharmakon1600-01506085, ALBB-025740, HY-N0132, Tox21_110390, Tox21_200962, Tox21_501085, ( inverted question mark)-Synephrine, BBL015111, BDBM50102660, NSC170956, NSC759316, PDSP1_000167, PDSP2_000166, s2362, 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, 1ST40086, 4-(1-Hydroxy-2-methylamino-ethyl)phenol, BP-12742, FS157243, 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, b-Methylamino-a-(4-hydroxyphenyl)ethyl alcohol, C04548, D07148, EN300-267997, S 0752, 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, 7336264B-EDC9-42C5-939B-FF800AB5BB4A, 202-300-9, 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, Parasympatol, DL-Synephrine, (+/-)-N-Methyloctopamine, benzenemethanol, 4-hydroxy-alpha-[(methylamino)methyl]-, 2,3-dihydroxybutanedioate (1:1) (salt)
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 52.5
Hydrogen Bond Donor Count 3.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCCCC1
Np Classifier Class Phenylethylamines
Deep Smiles CNCCcccccc6))O)))))O
Heavy Atom Count 12.0
Classyfire Class Phenols
Description Synephrine (or oxedrine) is a drug commonly used for weight loss. While its effectiveness is widely debated, synephrine has gained significant popularity as an alternative to ephedrine, a related substance which has been made illegal or restricted in many countries due to its use as a precursor in the illicit manufacture of methamphetamine. Products containing bitter orange or synephrine: suspected cardiovascular adverse reactions [citation needed]. Synephrine is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi., There has been some confusion surrounding synephrine and phenylephrine (neosynephrine), one of its positional isomers. The chemicals are similar in structure, the only difference is the location of the aromatic hydroxyl group. In synephrine, the hydroxyl is at the para position, whereas, in neosynephrine, it is at the meta position. Each compound has differing biological properties., p-Synephrine is an endogenous amine in plasma, in variable levels with a tendency to be higher in hypertensive patients (PMID 8255371).
Scaffold Graph Node Level C1CCCCC1
Classyfire Subclass 1-hydroxy-2-unsubstituted benzenoids
Isotope Atom Count 0.0
Molecular Complexity 122.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id P08913, P18089, P08908, Q16637, Q9NUW8, P00352, P00811, P54132, P08482, P40225, O89049, Q96KQ7, Q12809, P37231, O94925, P43220, P10145, P51449, n.a., P15289, Q9NR56, Q9GZQ4, O95342, P0DTD1, Q03181
Iupac Name 4-[1-hydroxy-2-(methylamino)ethyl]phenol
Prediction Hob 1.0
Class Phenols
Veber Rule True
Classyfire Superclass Benzenoids
Target Id NPT92, NPT93, NPT50, NPT94, NPT58, NPT96, NPT107
Xlogp -0.6
Superclass Benzenoids
Subclass 1-hydroxy-2-unsubstituted benzenoids
Gsk 4 400 Rule True
Molecular Formula C9H13NO2
Scaffold Graph Node Bond Level c1ccccc1
Prediction Swissadme 1.0
Inchi Key YRCWQPVGYLYSOX-UHFFFAOYSA-N
Silicos It Class Soluble
Fcsp3 0.3333333333333333
Logs -1.928
Rotatable Bond Count 3.0
State Solid
Logd 0.174
Synonyms &alpha, -(4-hydroxyphenyl)ethyl alcohol, 1-(p-Hydroxyphenyl)-2-methylaminoethanol, 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, 9CI, Analeptin, Ethaphene, Oxedrine, BAN, p-(a-Hydroxy-b-methylaminoethyl)phenol, Simpalon, Sympathol, (+/-)-synephrine, 1-(4-Hydroxyphenyl)-2-(methylamino)ethanol, 1-(4-Hydroxyphenyl)-2-methylaminoethanol, 4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol, beta-Methylamino-alpha-(4-hydroxyphenyl)ethyl alcohol, Oxedrine, p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcohol, Sympatol, -Synephrine, 4-Hydroxy-a-[(methylamino)methyl]benzenemethanol, 4-Hydroxy-α-[(methylamino)methyl]benzenemethanol, b-Methylamino-a-(4-hydroxyphenyl)ethyl alcohol, Β-methylamino-α-(4-hydroxyphenyl)ethyl alcohol, p-Hydroxy-a-[(methylamino)methyl]benzyl alcohol, p-Hydroxy-α-[(methylamino)methyl]benzyl alcohol, (+)-P-Synephrine, (+)-Synephrine, (+)-[(methylamino)Methyl]-benzenemethano, Parasympatol, Simpatol, Sympaethamin, Sympaethamine, Synephrine, Synephrin, synephrine
Esol Class Very soluble
Functional Groups CNC, CO, cO
Compound Name Synephrine
Kingdom Organic compounds
Prediction Hob Swissadme 1.0
Exact Mass 167.095
Formal Charge 0.0
Monoisotopic Mass 167.095
Hydrogen Bond Acceptor Count 3.0
Molecular Weight 167.2
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 1.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -0.6580895999999998
Inchi InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
Smiles CNCC(C1=CC=C(C=C1)O)O
Nring 1.0
Np Classifier Biosynthetic Pathway Alkaloids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent 1-hydroxy-2-unsubstituted benzenoids
Np Classifier Superclass Tyrosine alkaloids