Myristicin

Names

[ CAS No. ]:
607-91-0

[ Name ]:
Myristicin

[Synonym ]:
myristicine
4-methoxy-6-prop-2-en-1-yl-1,3-benzodioxole
6-Allyl-4-methoxy-1,3-benzodioxole
1,3-Benzodioxole, 4-methoxy-6-(2-propen-1-yl)-
MFCD00133549
Myristicin
4-Méthoxy-6-(2-propèn-1-yl)-1,3-benzodioxole
3-methoxy-4,5-methylenedioxyallylbenzene
1-allyl-4,5-methylenedioxy-3-methoxybenzene
EINECS 210-146-9

Biological Activity

[Description]:

Myristicine act as a serotonin receptor antagonist, a weak monamine oxidase (MAO) inhibitor. Myristicine is the main component of nutmeg essential oil from Myristica fragrans Houtt. Myristicine abuse produce hallucinogenic effects, organ damage, deliriumand others[1].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[References]

[1]. Kalbhen DA, et al. Nutmeg as a narcotic. A contribution to the chemistry and pharmacology of nutmeg (Myristica fragrans).Angew Chem Int Ed Engl. 1971 Jun;10(6):370-4.

[2]. Dawidowicz AL, et al. Simple and rapid determination of myristicin in human serum.Forensic Toxicol. 2013 Jan;31(1):119-123. Epub 2012 Aug 15.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
276.5±0.0 °C at 760 mmHg

[ Melting Point ]:
<-20ºC

[ Molecular Formula ]:
C₁₁H₁₂O₃

[ Molecular Weight ]:
192.211

[ Flash Point ]:
89.8±16.0 °C

[ Exact Mass ]:
192.078644

[ PSA ]:
27.69000

[ LogP ]:
3.26

[ Appearance of Characters ]:
oil | clear, light yellow

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.540

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CY2625000

CHEMICAL NAME :: Benzene, 5-allyl-1-methoxy-2,3-(methylenedioxy)-

CAS REGISTRY NUMBER :: 607-91-0

BEILSTEIN REFERENCE NO. :: 0166218

LAST UPDATED :: 199709

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C11-H12-O3

MOLECULAR WEIGHT :: 192.23

WISWESSER LINE NOTATION :: T56 BO DO CHJ FO1 H2U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 5700 ug/kg

TOXIC EFFECTS :: Behavioral - wakefulness Behavioral - euphoria Behavioral - hallucinations, distorted perceptions

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4260 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Behavioral - general anesthetic Liver - fatty liver degeneration

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Liver - other changes Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Liver - other changes Nutritional and Gross Metabolic - body temperature decrease

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 5,1613,1984

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361f-H412

[ Precautionary Statements ]:
P201-P273-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R52/53

[ Safety Phrases ]:
S61

[ RIDADR ]:
UN 3082 9/PG 3

[ WGK Germany ]:
1

[ RTECS ]:
CY2625000

[ Hazard Class ]:
9.0

[ HS Code ]:
2932999099

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Myristicin from nutmeg induces apoptosis via the mitochondrial pathway and down regulates genes of the DNA damage response pathways in human leukaemia K562 cells.

Chem. Biol. Interact. 218 , 1-9, (2014)

Myristicin, an allylbenzene, is a major active component of various spices, such as nutmeg and cinnamon, plants from the Umbelliferae family or in some essential oils, such as oils of clove or marjora...

Toxicological actions of plant-derived and anthropogenic methylenedioxyphenyl-substituted chemicals in mammals and insects.

J. Toxicol. Environ. Health. B. Crit. Rev. 15(6) , 365-95, (2012)

The methylenedioxyphenyl (MDP) substituent is a structural feature present in many plant chemicals that deter foraging by predatory insects and herbivores. With increasing use of herbal extracts in al...

GC/GC-MS analysis, isolation and identification of bioactive essential oil components from the Bhutanese medicinal plant, Pleurospermum amabile.

Nat. Prod. Commun. 8(9) , 1305-8, (2013)

We have hydrodistilled the essential oil (EO) from the aerial parts of the Bhutanese medicinal plant, Pleurospermum amabile using a Clevenger apparatus and evaluated this EO by GC/GC-MS and NMR analys...