Sarcosine

HCID 1088

Basic information

CAS
107-97-1
Standard SMILES
CNCC(=O)O
InChIKey
FSYKKLYZXJSNPZ-UHFFFAOYSA-N
Molecular formula
C3H7NO2
Average molar mass
89.09 g/mol
Monoisotopic mass
89.04767846

Overview

Deliquescent crystals or powder. Has a sweetish taste. (NTP, 1992)

Names & identifiers

Preferred name
Sarcosine
IUPAC
2-(methylamino)acetic acid
English name
Sarcosine
Molecular formula
C3H7NO2
Molecular weight
89.09

Names & synonyms

sarcosine107-97-1N-methylglycine2-(methylamino)acetic acidSarcosinic acidMethylglycineGlycine, N-methyl-N-Methylaminoacetic acidMethylaminoacetic acid(Methylamino)acetic acidSarcosin(Methylamino)ethanoic acid
Show more names
SarH-SAR-OHSAR-OHN-ME-GLY-OHMethyl-glycocollH-MEGLY-OHCH3NHCH2COOH
Acetic acid, (methylamino)-(methylamino)acetateDTXSID1047025CHEBI:15611Methylaminoethanoic acidZ711V88R5FN MethylglycineSarcosylate, Magnesium

Database identifiers

CAS
107-97-1、25951-24-0、68411-97-2
PubChem CID
1088
DTXSID
DTXSID1047025
ChEMBL
CHEMBL304383
ChEBI
CHEBI:15611
UNII
Z711V88R5F
EC Number
203-538-6
Nikkaji
J5.067I

Properties

Computed structural properties

XLogP
-2.8
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 3 items

Cosmetic ingredients (Cocoyl Sarcosine) -> CIR (Cosmetic Ingredient Review)

Cleansing; Surfactant; Skin conditioning

Personal care product

LogP-2.78
Solubility · 3 items

greater than or equal to 100 mg/mL at 61 °F (NTP, 1992)

300.0 mg/mL

5.6 [ug/mL] (The mean of the results at pH 7.4)

Melting Point · 2 items

406 °F (Decomposes) (NTP, 1992)

208 °C

Physicochemical properties

Melting point
208 · 208-212 °C (dec.)(lit.)
Boiling point
165.17 °C · 165.17°C (rough estimate)
Density
1.1948 · 1.1948 (rough estimate)
bulk density
600 kg/m3 · 600kg/m3
refractive index
1.4368 · 1.4368 (estimate)
Flash point
100 ℃ · >100℃

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 98.7% (149 of 151) of all reports.

Not Classified

Aggregated GHS information provided per 151 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: Glycine, N-methyl-

Status: Active Update: 20-12-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18702

Glycine, N-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Hazards SummaryCauses analgesia in acute intravenous studies of mice; [RTECS] May cause irritation; [Alfa Aesar MSDS]
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 item

SARCOSINE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical is incompatible with acids. (NTP, 1992).

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Treatment · 1 item

Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 2 items

Acyl sarcosines may cause irritation to the skin and eyes. They may also react to produce N-nitrososarcosine, which is believed to be carcinogenic. (A2881)

Acute Exposure: Can lead to eye and skin irritation. Chronic Exposure: High levels of sarcosine in prostate tissues are associated with aggressive prostate tumors. In this regard, sarcosine appears to function as an oncometabolite. High levels of sarcosine are also seen in patients with sarcosinemia. Sarcosinemia is a rare inborn error of metabolism that is characterized by an increased level of sarcosine (N-methylglycine) in the plasma and urine. The enzymatic block results from a deficiency of sarcosine dehydrogenase (SarDH), a liver mitochondrial matrix enzyme that converts sarcosine into glycine. The disease is mostly characterized by mental delay, cardiomyopathy, deafness and visual disturbance.

Exposure Routes · 2 items

Oral (A2881) ; inhalation (A2881) ; dermal (A2881)

Endogenous, Eye contact, Ingestion.

Toxicity Summary · 4 items

The CIR Expert Panel concluded that the following ingredients are safe as used in cosmetics when formulated to be non-irritating. The Expert Panel cautions that these ingredients should not be used in cosmetic products in which N-nitroso compounds can be found...Cocoyl Sarcosine...

Safe for use in cosmetics, with qualifications

While acyl sarcosines themselves are not toxic, they are nitrosating agents. Nitrosating agents may decompose and/or react to cause nitrosamine contamination. Nitrosamines are produced from secondary amines and amides in the presence of nitrite ions and are believed to be carcinogenic. The particular nitrosamine produced by acyl sarcosines is N-nitrososarcosine. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. They are then believed to induce their carcinogenic effects by forming DNA adducts at the N- and O-atoms. (L1889, L1890, A2878, A2879, A2880, A2881)

Sarcosine is an oncometabolite. Sarcosine appears to upregulate the expression of the potent oncoprotein called human epidermal growth factor receptor 2 (HER2/neu) in androgen-dependent prostate cancer cells upon exposure to exogenous sarcosine. Thus, sarcosine may induce prostate cancer progression by increased HER2/neu expression.

Signs and Symptoms · 2 items

Acyl sarcosines may cause irritation to the skin and eyes. (A2881)

Acute Exposure: eye irritation and skin irritation Chronic Exposure: sarcosinemia is associated with mental delay, cardiomyopathy, deafness and visual disturbance. In individuals with prostate cancer, high prostate tissue levels of sarcosine promote aggressive, rapidly growing prostate tumors.

Carcinogen Classification · 2 items

No indication of carcinogenicity (not listed by IARC). (L135)

Not listed by IARC. Has been implicated in oncogenesis (A15089).

Safety data

F
3
PPE
Eyeshields, Gloves, type N95 (US)
wgk
1
tsca
TSCA listed
rtecs
VQ2897000
hs_code
29224995

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Acyl sarcosines can be absorbed following oral or dermal contact, while nitrosamines can enter the body via ingestion, inhalation, or dermal contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, which essentially activates them into carcinogens. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase. (A2878, A2879, L1892)

Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine.

Tissue LocationsProstate
Cellular LocationsExtracellular
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency

Uses & manufacturing

Uses · 4 items

CIR ingredient: Cocoyl Sarcosine

Used as an intermediate in synthesis of toothpaste antienzyme agents; [Merck Index] An amino acid intermediate in the metabolism of choline. [ChemIDplus] Used to make antienzyme agents for cosmetics and pharmaceuticals; [NTP]

Acyl sarcosines are used as hair-conditioning agents and surfactant-cleansing agents in cosmetics, as well as to improve wetting and penetration of topical pharmaceutical products. Acyl sarcosines and their sodium salts are also used in the metal finishing and processing industries for their crystal modifying, anti-rust, and anti-corrosion properties. (A2881)

Sarcosine can be used as a cognitive enhancer and to treat schizophrenia.

Household ProductsInformation on 14 consumer products that contain Cocobetaine in the following categories is provided:
Use ClassificationCosmetics -> Cleansing; Surfactant; Skin conditioning
General Manufacturing InformationGlycine, N-methyl-: ACTIVE
Applications · 7 items

DescriptionSarcosine(cas:107-97-1) is the N-methyl derivative of glycine. It can be metabolized to the glycine through sarcosine dehydrogenase. It can be naturally found in many body tissues including muscles. In the laboratory, sarcosine could be synthesized through the reaction between chloroacetic acid and methylamine. Sarcosine is a potential interesting direction for the treatment of mental illness such as schizophrenia, possibly being related to its effect of increasing the glycine content in the brain, which increased the NMDA receptor activity. Sarcosine is also effective in the treatment of depression. Recent study has shown that sarcosine might be an important bio-marker for prostate cancer.

Usessarcosine is an intermediate in the production glycine from dietary consumption of choline. It is used in making toothpastes and biodegradable surfactants. Sarcosine can be found in foods such as vegetables, ham, egg yolks, turkey and legumes. The normal concentrations of sarcosine in human serum and in human urine are 1.4 µM and 1.6 µM respectively. Sarcosine has been observed to improve treatment of the mental illness known as schizophrenia: 2 g per day consumption of sarcosine (in addition to antipsychotic drug therapy) results in significant additional reductions not only both positive and negative symptoms, but also general psychopathological and neurocognitive symptoms. Sarcosine is thought to work by increasing glycine concentrations in the brain which causes increased NMDA receptor activation. Interestingly, consumption of sarcosine also reduced depressive symptoms in patients with schizophrenia. A clinical study showed sarcosine to be significantly more effective in treating major depression than the established antidepressant drug Citalopram.

UsesHas been found in starfish and sea urchins. It is used as intermediate in the synthesis of antienzyme agents for toothpaste. Found to be a marker for prostate cancer bioagression.

UsesSarcosine can improve people's intelligence, especially for exams such as the students need to temporarily increase the effectiveness of intelligence is more obvious. sarcosine can increase muscle strength and anaerobic explosiveness.To prevent damage caused by the brain injury. Sarcosine can effectively improve athletic performance,power, and shorten muscle recovery time.

Usessarcosine is a naturally occurring amino acid that is used in cosmetic formulations as a skin conditioner. There are some studies indicating that it is effective for oily skin. Its chemical name is n-methyl glycine.

UsesSarcosine is an important component for the production of the amino acid glycine and a byproduct of glycine breakdown. In the body, it is produced by converting dietary choline to glycine or breaking down methionine into glycine. It can also be synthesized in the laboratory with chloroacetic acid and methylamine. Sarcosine has a unique mild sweetness. Since a derivative of creatine helps prevent tooth decay and causes foam, it acts as an ingredient in toothpaste. Sarcosine can also be used as a drug, and research over the past 20 years has revealed its role in treating mental health disorders such as schizophrenia and depression.

General DescriptionDeliquescent crystals or powder. Has a sweetish taste.

Preparation methods · 1 item

PreparationSarcosine is prepared by boiling creatine with an aqueous solution of 10 times its weight of barium hydroxide until all odour of ammonia has disappeared. The creatine is decomposed into sarcosine and urea, the latter product being further split up into ammonia and carbonic acid.The excess of barium hydroxide is removed by a current of carbon dioxide, the liquid boiled, filtered, and evaporated to a syrup, from which the sarcosine is deposited in foliated crystals on standing. Sarcosine also results from the action of acids or alkalies on caffeine and theobromine (Vol.VI); and w. Paulmann (Arch. Pharm., 232, 601) recommends the hydrolysis of caffeine as the best method for the preparation of sarcosine, the yield being 60% of the theoretical.

Suppliers9 total

北京华美互利生物化工010-56205725 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
XIAMEN EQUATION CHEMICAL CO.,LTD+86-5926515854 +86-18060954864 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Sarcosine is a N-alkylglycine that is the N-methyl derivative of glycine. It is an intermediate in the metabolic pathway of glycine. It has a role as a glycine transporter 1 inhibitor, a glycine receptor agonist, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a N-alkylglycine, a N-methyl-amino acid and a member of N-methylglycines. It is a conjugate base of a sarcosinium. It is a conjugate acid of a sarcosinate. It is a tautomer of a sarcosine zwitterion.

Related reactions

724 records

Compound notes

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