Octopamine (drug)

For octopamine as an invertebrate neurotransmitter, see Octopamine (neurotransmitter).

Octopamine

Systematic (IUPAC) name
(RS)-4-(2-amino-1-hydroxy-ethyl)phenol
Clinical data
Legal status	Rx / Uncontrolled / Banned by World Anti-Doping Agency
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	99.42 %
Metabolism	p-hydroxymandelic acid (if p-octopamine) or m-hydroxymandelic acid (if m-octopamine
Biological half-life	15 minutes in insects. Between 76 and 175 minutes in humans
Excretion	Up to 93% of ingested octopamine is eliminated via the urinary route within 24 hours
Identifiers
CAS Number	104-14-3 Y
ATC code	C01CA18 (WHO)
PubChem	CID: 4581
IUPHAR/BPS	2149
ChemSpider	4420 Y
UNII	14O50WS8JD Y
ChEBI	CHEBI:17134 N
ChEMBL	CHEMBL53929 Y
Synonyms	Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine
Chemical data
Formula	C8H11NO2
Molecular mass	153.178 g/mol
SMILES OC(c1ccc(O)cc1)CN
InChI InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2 Y Key:QHGUCRYDKWKLMG-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Octopamine (molecular formula C₈H₁₁NO₂) is an organic chemical closely related to norepinephrine. In many types of invertebrates it functions as an important neurotransmitter and hormone, but in the human body it normally exists only at trace levels and has no known function. Because it shares some of the actions of norepinephrine, octopamine has been sold under trade names such as Epirenor, Norden, and Norfen for use as a sympathomimetic drug, available by prescription. Very little information exists concerning its clinical usefulness or safety.

In mammals, octopamine may mobilize the release of fat from adipocytes (fat cells), which has led to its promotion on the internet as a slimming aid. However, the released fat is likely to be promptly taken up into other cells, and there is no evidence that octopamine facilitates weight loss. Octopamine may also increase blood pressure significantly when combined with other stimulants, as in some weight loss supplements.