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 |
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FOUND_INto/from Gratiola Officinalis (Plant) Rel Props:Reference: - 128. Outgoing r'ship
FOUND_INto/from Gynochthodes Officinalis (Plant) Rel Props:Reference: - 129. Outgoing r'ship
FOUND_INto/from Habenaria Intermedia (Plant) Rel Props:Reference: - 130. Outgoing r'ship
FOUND_INto/from Hertia Intermedia (Plant) Rel Props:Reference: - 131. Outgoing r'ship
FOUND_INto/from Hyssopus Officinalis (Plant) Rel Props:Reference: - 132. Outgoing r'ship
FOUND_INto/from Incarvillea Sinensis (Plant) Rel Props:Reference: - 133. Outgoing r'ship
FOUND_INto/from Juglans Sinensis (Plant) Rel Props:Reference: - 134. Outgoing r'ship
FOUND_INto/from Kopsia Officinalis (Plant) Rel Props:Reference: - 135. Outgoing r'ship
FOUND_INto/from Lappula Intermedia (Plant) Rel Props:Reference: - 136. Outgoing r'ship
FOUND_INto/from Laricifomes Officinalis (Plant) Rel Props:Reference: - 137. Outgoing r'ship
FOUND_INto/from Lavandula Intermedia (Plant) Rel Props:Reference: - 138. Outgoing r'ship
FOUND_INto/from Lavandula Officinalis (Plant) Rel Props:Reference: - 139. Outgoing r'ship
FOUND_INto/from Leptadenia Reticulata (Plant) Rel Props:Reference: - 140. Outgoing r'ship
FOUND_INto/from Libanotis Intermedia (Plant) Rel Props:Reference: - 141. Outgoing r'ship
FOUND_INto/from Ligularia Intermedia (Plant) Rel Props:Reference: - 142. Outgoing r'ship
FOUND_INto/from Macaranga Sinensis (Plant) Rel Props:Reference: - 143. Outgoing r'ship
FOUND_INto/from Magnolia Officinalis (Plant) Rel Props:Reference: - 144. Outgoing r'ship
FOUND_INto/from Mandragora Officinalis (Plant) Rel Props:Reference: - 145. Outgoing r'ship
FOUND_INto/from Melilotus Officinalis (Plant) Rel Props:Reference: - 146. Outgoing r'ship
FOUND_INto/from Melissa Officinalis (Plant) Rel Props:Reference: - 147. Outgoing r'ship
FOUND_INto/from Menyanthes Trifoliata (Plant) Rel Props:Reference: - 148. Outgoing r'ship
FOUND_INto/from Miliusa Sinensis (Plant) Rel Props:Reference: - 149. Outgoing r'ship
FOUND_INto/from Millettia Reticulata (Plant) Rel Props:Reference: - 150. Outgoing r'ship
FOUND_INto/from Miscanthus Sinensis (Plant) Rel Props:Reference: - 151. Outgoing r'ship
FOUND_INto/from Morinda Reticulata (Plant) Rel Props:Reference: - 152. Outgoing r'ship
FOUND_INto/from Myristica Officinalis (Plant) Rel Props:Reference: - 153. Outgoing r'ship
FOUND_INto/from Nauclea Officinalis (Plant) Rel Props:Reference: - 154. Outgoing r'ship
FOUND_INto/from Neottia Sinensis (Plant) Rel Props:Reference: - 155. Outgoing r'ship
FOUND_INto/from Nyssa Sinensis (Plant) Rel Props:Reference: - 156. Outgoing r'ship
FOUND_INto/from Othonna Intermedia (Plant) Rel Props:Reference: - 157. Outgoing r'ship
FOUND_INto/from Paeonia Officinalis (Plant) Rel Props:Reference: - 158. Outgoing r'ship
FOUND_INto/from Petasites Officinalis (Plant) Rel Props:Reference: - 159. Outgoing r'ship
FOUND_INto/from Phellodendron Amurense (Plant) Rel Props:Reference: - 160. Outgoing r'ship
FOUND_INto/from Photinia Bodinieri (Plant) Rel Props:Reference: - 161. Outgoing r'ship
FOUND_INto/from Pimenta Officinalis (Plant) Rel Props:Reference: - 162. Outgoing r'ship
FOUND_INto/from Plathymenia Reticulata (Plant) Rel Props:Reference: - 163. Outgoing r'ship
FOUND_INto/from Pogostemon Auricularis (Plant) Rel Props:Reference: - 164. Outgoing r'ship
FOUND_INto/from Pogostemon Auricularius (Plant) Rel Props:Reference: - 165. Outgoing r'ship
FOUND_INto/from Pogostemon Benghalense (Plant) Rel Props:Reference: - 166. Outgoing r'ship
FOUND_INto/from Pogostemon Benghalensis (Plant) Rel Props:Reference: - 167. Outgoing r'ship
FOUND_INto/from Pogostemon Cablin (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 168. Outgoing r'ship
FOUND_INto/from Pogostemon Heyneanus (Plant) Rel Props:Reference: - 169. Outgoing r'ship
FOUND_INto/from Pogostemon Paniculatus (Plant) Rel Props:Reference: - 170. Outgoing r'ship
FOUND_INto/from Pogostemon Parviflorus (Plant) Rel Props:Reference: - 171. Outgoing r'ship
FOUND_INto/from Pogostemon Patchouli (Plant) Rel Props:Reference: - 172. Outgoing r'ship
FOUND_INto/from Pogostemon Plectranthoides (Plant) Rel Props:Reference: - 173. Outgoing r'ship
FOUND_INto/from Pogostemon Pubescens (Plant) Rel Props:Reference: - 174. Outgoing r'ship
FOUND_INto/from Pogostemon Purpurascens (Plant) Rel Props:Reference: - 175. Outgoing r'ship
FOUND_INto/from Pogostemon Rugosus (Plant) Rel Props:Reference: - 176. Outgoing r'ship
FOUND_INto/from Pogostemon Stellatus (Plant) Rel Props:Reference: - 177. Outgoing r'ship
FOUND_INto/from Pogostemon Vestitus (Plant) Rel Props:Reference: - 178. Outgoing r'ship
FOUND_INto/from Pothos Officinalis (Plant) Rel Props:Reference: - 179. Outgoing r'ship
FOUND_INto/from Pseudotsuga Sinensis (Plant) Rel Props:Reference: - 180. Outgoing r'ship
FOUND_INto/from Ptelea Trifoliata (Plant) Rel Props:Reference: - 181. Outgoing r'ship
FOUND_INto/from Pterocarpus Officinalis (Plant) Rel Props:Reference: - 182. Outgoing r'ship
FOUND_INto/from Radermachera Sinica (Plant) Rel Props:Reference: - 183. Outgoing r'ship
FOUND_INto/from Rosmarinus Officinalis (Plant) Rel Props:Reference: - 184. Outgoing r'ship
FOUND_INto/from Saccharum Sinensis (Plant) Rel Props:Reference: - 185. Outgoing r'ship
FOUND_INto/from Sacia Reticulata (Plant) Rel Props:Reference: - 186. Outgoing r'ship
FOUND_INto/from Salacia Reticulata (Plant) Rel Props:Reference: - 187. Outgoing r'ship
FOUND_INto/from Salvia Officinalis (Plant) Rel Props:Reference: - 188. Outgoing r'ship
FOUND_INto/from Salvia Sinica (Plant) Rel Props:Reference: - 189. Outgoing r'ship
FOUND_INto/from Sanguisorba Officinalis (Plant) Rel Props:Reference: - 190. Outgoing r'ship
FOUND_INto/from Saponaria Officinalis (Plant) Rel Props:Reference: - 191. Outgoing r'ship
FOUND_INto/from Sassafras Officinalis (Plant) Rel Props:Reference: - 192. Outgoing r'ship
FOUND_INto/from Schefflera Bodinieri (Plant) Rel Props:Reference: - 193. Outgoing r'ship
FOUND_INto/from Schisandra Propinqua (Plant) Rel Props:Reference: - 194. Outgoing r'ship
FOUND_INto/from Scindapsus Officinalis (Plant) Rel Props:Reference: - 195. Outgoing r'ship
FOUND_INto/from Scopolia Sinensis (Plant) Rel Props:Reference: - 196. Outgoing r'ship
FOUND_INto/from Selaginella Sinensis (Plant) Rel Props:Reference: - 197. Outgoing r'ship
FOUND_INto/from Spiranthes Sinensis (Plant) Rel Props:Reference: - 198. Outgoing r'ship
FOUND_INto/from Stephania Sinica (Plant) Rel Props:Reference: - 199. Outgoing r'ship
FOUND_INto/from Styrax Officinalis (Plant) Rel Props:Reference: - 200. Outgoing r'ship
FOUND_INto/from Tetradium Fraxinifolium (Plant) Rel Props:Reference: - 201. Outgoing r'ship
FOUND_INto/from Tetradium Glabrifolium (Plant) Rel Props:Reference: - 202. Outgoing r'ship
FOUND_INto/from Tetradium Ruticarpum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 203. Outgoing r'ship
FOUND_INto/from Tetradium Trichotomum (Plant) Rel Props:Reference: - 204. Outgoing r'ship
FOUND_INto/from Tinospora Sinensis (Plant) Rel Props:Reference: - 205. Outgoing r'ship
FOUND_INto/from Toona Sinensis (Plant) Rel Props:Reference: - 206. Outgoing r'ship
FOUND_INto/from Uncaria Sinensis (Plant) Rel Props:Reference: - 207. Outgoing r'ship
FOUND_INto/from Utricularia Reticulata (Plant) Rel Props:Reference: - 208. Outgoing r'ship
FOUND_INto/from Valeriana Officinalis (Plant) Rel Props:Reference: - 209. Outgoing r'ship
FOUND_INto/from Verbena Officinalis (Plant) Rel Props:Reference: - 210. Outgoing r'ship
FOUND_INto/from Walsura Trifoliata (Plant) Rel Props:Reference: - 211. Outgoing r'ship
FOUND_INto/from Wisteria Sinensis (Plant) Rel Props:Reference: