Synonym
Octopamine HCl; Octopamine HCl salt; Octopamine Hydrochloride; Octopamine Hydrochloride salt;
IUPAC/Chemical Name
4-(2-Amino-1-hydroxyethyl)phenol hydrochloride
InChi Key
PUMZXCBVHLCWQG-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H11NO2.ClH/c9-5-8(11)6-1-3-7(10)4-2-6;/h1-4,8,10-11H,5,9H2;1H
SMILES Code
OC1=CC=C(C(O)CN)C=C1.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Octopamine ((±)-p-Octopamine) hydrochloride, a biogenic monoamine structurally related to noradrenaline, acts as a neurohormone, a neuromodulator and a neurotransmitter in invertebrates.
In vitro activity:
he effects of octopamine and the catecholamines on the decrease in cyclic AMP production were additive at submaximal concentrations, whilst octopamine reduced the stimulant effect of submaximal concentrations of noradrenaline on cyclic AMP production after pertussis toxin pretreatment. The time courses of the inhibitory effects of both meta-octopamine and noradrenaline were parallel and peaked after a 1 min exposure to the agonist.
Reference: Br J Pharmacol. 1997 Sep;122(2):191-8. https://pubmed.ncbi.nlm.nih.gov/9313925/
In vivo activity:
The lipolytic effect and the counter-regulation of insulin action on glucose transport provoked by 0.1 to 1 mM octopamine or by 1 microM beta3-AR agonists found in control animals disappeared in adipocytes from beta3-AR-deficient mice. This revealed an insulin-like effect of octopamine on glucose uptake, which was dependent on its oxidation by MAO or SSAO, as was the case for tyramine and benzylamine, devoid of beta3-adrenergic agonism.
Reference: J Pharmacol Exp Ther. 2001 Oct;299(1):96-104. https://pubmed.ncbi.nlm.nih.gov/11561068/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
12.0 |
63.28 |
| DMSO |
50.0 |
263.66 |
| Ethanol |
10.5 |
55.37 |
| PBS (pH 7.2) |
10.0 |
52.73 |
| Water |
44.0 |
232.02 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
189.64
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hoshikawa H, Uno M, Honjoh S, Nishida E. Octopamine enhances oxidative stress resistance through the fasting-responsive transcription factor DAF-16/FOXO in C. elegans. Genes Cells. 2017 Feb;22(2):210-219. doi: 10.1111/gtc.12469. Epub 2017 Jan 20. PMID: 28105749.
2. Airriess CN, Rudling JE, Midgley JM, Evans PD. Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor. Br J Pharmacol. 1997 Sep;122(2):191-8. doi: 10.1038/sj.bjp.0701348. PMID: 9313925; PMCID: PMC1564916.
3. Schendzielorz T, Schirmer K, Stolte P, Stengl M. Octopamine regulates antennal sensory neurons via daytime-dependent changes in cAMP and IP3 levels in the hawkmoth Manduca sexta. PLoS One. 2015 Mar 18;10(3):e0121230. doi: 10.1371/journal.pone.0121230. PMID: 25785721; PMCID: PMC4364694.
4. Visentin V, Morin N, Fontana E, Prévot D, Boucher J, Castan I, Valet P, Grujic D, Carpéné C. Dual action of octopamine on glucose transport into adipocytes: inhibition via beta3-adrenoceptor activation and stimulation via oxidation by amine oxidases. J Pharmacol Exp Ther. 2001 Oct;299(1):96-104. PMID: 11561068.
In vitro protocol:
1. Hoshikawa H, Uno M, Honjoh S, Nishida E. Octopamine enhances oxidative stress resistance through the fasting-responsive transcription factor DAF-16/FOXO in C. elegans. Genes Cells. 2017 Feb;22(2):210-219. doi: 10.1111/gtc.12469. Epub 2017 Jan 20. PMID: 28105749.
2. Airriess CN, Rudling JE, Midgley JM, Evans PD. Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor. Br J Pharmacol. 1997 Sep;122(2):191-8. doi: 10.1038/sj.bjp.0701348. PMID: 9313925; PMCID: PMC1564916.
In vivo protocol:
1. Schendzielorz T, Schirmer K, Stolte P, Stengl M. Octopamine regulates antennal sensory neurons via daytime-dependent changes in cAMP and IP3 levels in the hawkmoth Manduca sexta. PLoS One. 2015 Mar 18;10(3):e0121230. doi: 10.1371/journal.pone.0121230. PMID: 25785721; PMCID: PMC4364694.
2. Visentin V, Morin N, Fontana E, Prévot D, Boucher J, Castan I, Valet P, Grujic D, Carpéné C. Dual action of octopamine on glucose transport into adipocytes: inhibition via beta3-adrenoceptor activation and stimulation via oxidation by amine oxidases. J Pharmacol Exp Ther. 2001 Oct;299(1):96-104. PMID: 11561068.
1: Li LB, Cui XN, Reith MA. Is Na(+) required for the binding of dopamine, amphetamine, tyramine, and octopamine to the human dopamine transporter? Naunyn Schmiedebergs Arch Pharmacol. 2002 Apr;365(4):303-11. Epub 2002 Feb 20. PubMed PMID: 11919655.
2: Kirschbaum J, Rebscher K, Brückner H. Liquid chromatographic determination of biogenic amines in fermented foods after derivatization with 3,5-dinitrobenzoyl chloride. J Chromatogr A. 2000 Jun 9;881(1-2):517-30. PubMed PMID: 10905732.
3: Capasso A, Carginale V, Madonna L, Mancaniello D, Scudiero R, Paolo De Prisco P, De Petrocellis B, Parisi E. A dopamine- and octopamine-sensitive adenylate cyclase in the nervous system of Octopus vulgaris. Comp Biochem Physiol B. 1991;100(4):805-8. PubMed PMID: 1782763.
4: Baraldi M, Zeneroli ML, Ricci P, Caselgrandi E, Ventura E. Down regulation of striatal dopamine receptors in experimental hepatic encephalopathy. Life Sci. 1983 Mar 28;32(13):1417-25. PubMed PMID: 6403789.
5: Laven R, Schäfer EA. [Release of norfenefrine from sustained-release formulations by an in vitro dissolution model. Simulation of "drug levels" by calculation using pharmacokinetical constants and comparison with in vivo course of action (author's transl)]. Arzneimittelforschung. 1981;31(2):353-6. German. PubMed PMID: 7194653.
6: HEINECKER R, NANAY I. [ON THE EFFECT OF MONOAMINE OXIDASE INHIBITORS (MAOI) ON THE EFFECT OF ORALLY ADMINISTERED M-HYDROXY-1-PHENYL-2-AMINOETHANOL HCL (NOVADRAL) ON THE BLOOD CIRCULATION]. Arch Kreislaufforsch. 1963 Dec;42:63-84. German. PubMed PMID: 14116199.
