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O0250

Sigma-Aldrich

(±)-Octopamine hydrochloride

≥95%, solid

Synonym(s):

α-(Aminomethyl)-4-hydroxybenzyl alcohol hydrochloride, (±)-1-(4-Hydroxyphenyl)-2-amino­ethanol hydrochloride

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$143.00
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1 G
$62.60
5 G
$143.00
10 G
$248.00

About This Item

Linear Formula:
HOC6H4CH(CH2NH2)OH · HCl
CAS Number:
770-05-8
Molecular Weight:
189.64
Beilstein/REAXYS Number:
3915414
EC Number:
212-216-4
MDL number:
MFCD00012881
UNSPSC Code:
12352116
PubChem Substance ID:
24277791
NACRES:
NA.32

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assay

≥95%

form

solid

color

white to off-white

mp

~170 °C (dec.) (lit.)

solubility

H2O: soluble

SMILES string

Cl[H].NCC(O)c1ccc(O)cc1

InChI

1S/C8H11NO2.ClH/c9-5-8(11)6-1-3-7(10)4-2-6;/h1-4,8,10-11H,5,9H2;1H

InChI key

PUMZXCBVHLCWQG-UHFFFAOYSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152)

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General description

Octopamine is a biogenic amine, which functions as a neurotransmitter, neuromodulator and neurohormone.[1] It is used to regulate various behaviors, such as learning, memory and aggression.[2] Octopamine is present in mammalian tissues, human urine and invertebrates.[3]

Application

(±)-Octopamine hydrochloride has been used:
  • for neurotransmitter assays[4]
  • to rupture the encased oocyte into the oviduct[5]
  • to specifically induce dramatic assembly of reflectin[6]
  • to identify central octopamine receptor-expressing neurons (OARNs) involved in aggression in Drosophila[7]

Biochem/physiol Actions

α-adrenoceptor agonist; invertebrate neurotransmitter.

Caution

hygroscopic - handle under Argon

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL1279
WXBF1751V
BCCH0825
BCCF1039
BCCC0656

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T Roeder
Progress in neurobiology, 59(5), 533-561 (1999-10-09)
Octopamine (OA), a biogenic monoamine structurally related to noradrenaline, acts as a neurohormone, a neuromodulator and a neurotransmitter in invertebrates. It is present in relatively high concentrations in neuronal as well as in non-neuronal tissues of most invertebrate species studied.
Origin of the reflectin gene and hierarchical assembly of its protein
Guan Z, et al.
Current Biology, 27(18), 2833-2842 (2017)
Characterization of a beta-adrenergic-like octopamine receptor from the rice stem borer (Chilo suppressalis)
Wu SF, et al.
The Journal of Experimental Biology, 215(15), 2646-2652 (2012)
A circuit node that integrates convergent input from neuromodulatory and social behavior-promoting neurons to control aggression in Drosophila
Watanabe K, et al.
Neuron, 95(5), 1112-1128 (2017)
Octopamine controls starvation resistance, life span and metabolic traits in Drosophila
Li Y, et al.
Scientific reports, 6, 35359-35359 (2016)
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Chromatograms

application for HPLC

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