(3-Carboxypropyl)trimethylammonium chloride

Names

[ Name ]:
(3-Carboxypropyl)trimethylammonium chloride

[Synonym ]:
g-Butyrobetaine Hydrochloride
3-Carboxy-N,N,N-trimethylpropan-1-aminium chloride
Trimethylaminobutyrate
3-carboxy-N,N,N-trimethylpropan-1-ammonium chloride
3-Carboxy-N,N,N-trimethyl-1-propanaminium chloride
(3-Carboxypropyl)trimethylammonium chloride
Butyrobetaine chloride
γ-Butyrobetaine hydrochloride
MFCD00011905
1-Propanaminium, 3-carboxy-N,N,N-trimethyl-, chloride (1:1)
Deoxycarnitine hydrochloride
3-carboxy-N,N,N-trimethylpropanaminium chloride

Biological Activity

[Description]:

(3-Carboxypropyl)trimethylammonium chloride is angiopathic substance produced as an intermediary metabolite by gut microbiota that feed on carnitine in dietary red meat.

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Research Areas >> Metabolic Disease

[In Vivo]

(3-Carboxypropyl)trimethylammonium chloride is produced as an intermediary metabolite by gut microbes of L-Carnitine to TMAO[1]. (3-Carboxypropyl)trimethylammonium chloride is implicated in arteriosclerosis and long-term cardiovascular death[2].

[References]

[1]. Koeth RA, et al. γ-Butyrobetaine is a proatherogenic intermediate in gut microbial metabolism of L-carnitine to TMAO. Cell Metab. 2014 Nov 4;20(5):799-812.

[2]. Susumu Ogawa, et al. The Dynamics of Carnitine, γ-butyrobetaine and Trimethylamine N-oxide in Diabetics and the Effects of Changes in Renal Function. Ogawa et al., J Nephrol Ren Dis 2017, 1:2

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
220ºC (dec.)(lit.)

[ Molecular Formula ]:
C₇H₁₆ClNO₂

[ Molecular Weight ]:
181.660

[ Exact Mass ]:
181.086960

[ PSA ]:
37.30000

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BP3850000

CHEMICAL NAME :: Ammonium, (3-carboxypropyl)trimethyl-, chloride

CAS REGISTRY NUMBER :: 6249-56-5

LAST UPDATED :: 199206

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C7-H15-N-O2.Cl

MOLECULAR WEIGHT :: 180.68

WISWESSER LINE NOTATION :: QV3K1&1&1 &Q &G

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - fluid intake Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 3,28,1959

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 475 mg/kg

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

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 145,233,1963

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ HS Code ]:
2923900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2923900090

[ Summary ]:
2923900090 other quaternary ammonium salts and hydroxides。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%