Domoic acid

Names

[ Name ]:
Domoic acid

[Synonym ]:
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline
L-Proline, 3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (3S,4S)-
Domoic acid,(2S,3S,4R,5'R)-2-Carboxy-4-(5'-carboxy-1'-methyl-1Z,3E-hexadienyl)-3-pyrrolidineaceticacid
[2S-[2a,3b,4b(1Z,3E,5S*)]]-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic Acid
Domoic acid
MFCD00040640
L-Domoic acid
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxy-2,4-heptadien-2-yl]-3-(carboxymethyl)-L-proline

Biological Activity

[Description]:

Domoic acid ((-)-Domoic acid; L-Domoic acid) is an excitatory neurotransmitter isolated from a form of marine vegetation, Nitzschia pungens[1]. Domoic acid produces neurotoxic effect through activating kainate receptor[2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[References]

[1]. T M Perl, et al. An outbreak of toxic encephalopathy caused by eating mussels contaminated with domoic acid. N Engl J Med. 1990 Jun 21;322(25):1775-80.

[2]. G Debonnel, et al. Domoic acid, the alleged "mussel toxin," might produce its neurotoxic effect through kainate receptor activation: an electrophysiological study in the dorsal hippocampus. Can J Physiol Pharmacol. 1989 Jan;67(1):29-33.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
607.2±55.0 °C at 760 mmHg

[ Melting Point ]:
228ºC

[ Molecular Formula ]:
C₁₅H₂₁NO₆

[ Molecular Weight ]:
311.330

[ Flash Point ]:
321.0±31.5 °C

[ Exact Mass ]:
311.136902

[ PSA ]:
123.93000

[ LogP ]:
0.61

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.545

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UX9665100

CHEMICAL NAME :: 3-Pyrrolidineacetic acid, 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-, (2S-(2-alpha,3- beta,4-beta(1Z,3E,5S*)))-

CAS REGISTRY NUMBER :: 14277-97-5

LAST UPDATED :: 199706

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C15-H21-N-O6

MOLECULAR WEIGHT :: 311.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 28,501,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 320 mg/kg/9W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 34,525,1996

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ RIDADR ]:
UX9665100

[ RTECS ]:
UX9665100

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Metal-organic framework UiO-66 modified magnetite@silica core-shell magnetic microspheres for magnetic solid-phase extraction of domoic acid from shellfish samples.

J. Chromatogr. A. 1400 , 10-8, (2015)

Fe3O4@SiO2@UiO-66 core-shell magnetic microspheres were synthesized and characterized by transmission electron microscopy, scanning electron microscopy, X-ray diffraction, Fourier transform infrared s...

The prostaglandin EP1 receptor potentiates kainate receptor activation via a protein kinase C pathway and exacerbates status epilepticus.

Neurobiol. Dis. 70 , 74-89, (2014)

Prostaglandin E2 (PGE2) regulates membrane excitability, synaptic transmission, plasticity, and neuronal survival. The consequences of PGE2 release following seizures has been the subject of much stud...

Ursolic acid improves domoic acid-induced cognitive deficits in mice.

Toxicol. Appl. Pharmacol. 271(2) , 127-36, (2013)

Our previous findings suggest that mitochondrial dysfunction is the mechanism underlying cognitive deficits induced by domoic acid (DA). Ursolic acid (UA), a natural triterpenoid compound, possesses m...