1.0 2010-04-08 22:04:57 UTC 2025-11-18 22:31:03 UTC FDB001397 Synephrine 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). α-(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 C9H13NO2 167.205 167.094628665 4-[1-hydroxy-2-(methylamino)ethyl]phenol synephrine 94-07-5 CNCC(O)C1=CC=C(O)C=C1 InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3 YRCWQPVGYLYSOX-UHFFFAOYSA-N belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 1-hydroxy-2-unsubstituted benzenoids Organic compounds Benzenoids Phenols 1-hydroxy-2-unsubstituted benzenoids Aromatic homomonocyclic compounds 1,2-aminoalcohols Aralkylamines Aromatic alcohols Benzene and substituted derivatives Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Secondary alcohols 1,2-aminoalcohol 1-hydroxy-2-unsubstituted benzenoid Alcohol Amine Aralkylamine Aromatic alcohol Aromatic homomonocyclic compound Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary aliphatic amine Secondary amine ethanolamines phenethylamine alkaloid phenols logp -0.62 ALOGPS logs -0.95 ALOGPS solubility 1.86e+01 g/l ALOGPS melting_point 184.5 oC logp -0.071 ChemAxon pka_strongest_acidic 9.76 ChemAxon pka_strongest_basic 9.15 ChemAxon iupac 4-[1-hydroxy-2-(methylamino)ethyl]phenol ChemAxon average_mass 167.205 ChemAxon mono_mass 167.094628665 ChemAxon smiles CNCC(O)C1=CC=C(O)C=C1 ChemAxon formula C9H13NO2 ChemAxon inchi InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3 ChemAxon inchikey YRCWQPVGYLYSOX-UHFFFAOYSA-N ChemAxon polar_surface_area 52.49 ChemAxon refractivity 47.25 ChemAxon polarizability 18.23 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2257 Specdb::MsIr 2258 Specdb::MsIr 2259 Specdb::CMs 1480 Specdb::CMs 11610 Specdb::CMs 31527 Specdb::CMs 31895 Specdb::CMs 31896 Specdb::CMs 31897 Specdb::CMs 38817 Specdb::CMs 165051 Specdb::NmrOneD 54662 Specdb::NmrOneD 54663 Specdb::NmrOneD 54664 Specdb::NmrOneD 54665 Specdb::NmrOneD 54666 Specdb::NmrOneD 54667 Specdb::NmrOneD 54668 Specdb::NmrOneD 54669 Specdb::NmrOneD 54670 Specdb::NmrOneD 54671 Specdb::NmrOneD 54672 Specdb::NmrOneD 54673 Specdb::NmrOneD 54674 Specdb::NmrOneD 54675 Specdb::NmrOneD 54676 Specdb::NmrOneD 54677 Specdb::NmrOneD 54678 Specdb::NmrOneD 54679 Specdb::NmrOneD 54680 Specdb::NmrOneD 54681 Specdb::MsMs 11219 Specdb::MsMs 11220 Specdb::MsMs 11221 Specdb::MsMs 17891 Specdb::MsMs 17892 Specdb::MsMs 17893 Specdb::MsMs 439576 Specdb::MsMs 439577 Specdb::MsMs 449640 Specdb::MsMs 449641 Specdb::MsMs 2229348 Specdb::MsMs 2230127 Specdb::MsMs 2252968 Specdb::MsMs 2253521 Specdb::MsMs 2255001 Specdb::MsMs 2255564 Specdb::MsMs 2256939 Specdb::MsMs 2257673 Specdb::MsMs 2258944 Specdb::MsMs 2259612 Specdb::MsMs 2441083 Specdb::MsMs 2441084 Specdb::MsMs 2441085 Specdb::MsMs 2524272 Specdb::MsMs 2524273 HMDB0004826 29081 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823