Methyl-n-amylnitrosamine

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Methyl-n-amylnitrosamine
Methylamylnitrosamine.png
Names
Preferred IUPAC name
Methyl(pentyl)nitrous amide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
MeSH N-amyl-N-methylnitrosamine
PubChem CID
UNII
  • InChI=1S/C6H14N2O/c1-3-4-5-6-8(2)7-9/h3-6H2,1-2H3 Yes check.svgY
    Key: KSFCDINBDBFFSI-UHFFFAOYSA-N Yes check.svgY
  • CCCCCN(C)N=O
Properties
C6H14N2O
Molar mass 130.191 g·mol−1
AppearanceYellow, transparent liquid
log P 1.542
Related compounds
Related amines
Related compounds
Agmatine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Methyl-n-amylnitrosamine (MNAN) is a potential carcinogen [1] It is metabolized in the liver by the enzyme CYP2A6.

Related Research Articles

A methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms — CH3. In formulas, the group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, it can be found on its own in any of three forms: anion, cation or radical. The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed.

Methyl isocyanate Chemical compound

Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane, methyl carbylamine and MIC. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides (such as carbaryl, carbofuran, methomyl, and aldicarb). It has also been used in the production of rubbers and adhesives. As a highly toxic and irritating material, it is extremely hazardous to human health. It was the principal toxicant involved in the Bhopal disaster, which killed 2,259 people initially and officially 20,000 people in total.

In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These terms are commonly used in chemistry, biochemistry, soil science, and the biological sciences.

Methyl radical Chemical compound

Methyl is an organic compound with the chemical formula CH
3
. It is a metastable colourless gas, which is mainly produced in situ as a precursor to other hydrocarbons in the petroleum cracking industry. It can act as either a strong oxidant or a strong reductant, and is quite corrosive to metals.

In organic chemistry, an alkyl substituent is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of CnH2n+1. A cycloalkyl is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula CnH2n-1. Typically an alkyl is a part of a larger molecule. In structural formula, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula CH3−.

Methyl salicylate Chemical compound

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer, but often associatively called "minty", as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. It is also produced synthetically, used as a fragrance and as a flavoring agent.

<i>Controlled Drugs and Substances Act</i> Canadian federal drug regulation act

The Controlled Drugs and Substances Act is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals the Narcotic Control Act and Parts III and IV of the Food and Drugs Act, and establishes eight Schedules of controlled substances and two Classes of precursors. It provides that "The Governor in Council may, by order, amend any of Schedules I to VIII by adding to them or deleting from them any item or portion of an item, where the Governor in Council deems the amendment to be necessary in the public interest."

Methylisopropyltryptamine

N-Methyl-N-isopropyltryptamine (MiPT) is a psychedelic tryptamine, closely related to DMT, DiPT and Miprocin.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

Methyltransferase Group of methylating enzymes

Methyltransferases are a large group of enzymes that all methylate their substrates but can be split into several subclasses based on their structural features. The most common class of methyltransferases is class I, all of which contain a Rossmann fold for binding S-Adenosyl methionine (SAM). Class II methyltransferases contain a SET domain, which are exemplified by SET domain histone methyltransferases, and class III methyltransferases, which are membrane associated. Methyltransferases can also be grouped as different types utilizing different substrates in methyl transfer reactions. These types include protein methyltransferases, DNA/RNA methyltransferases, natural product methyltransferases, and non-SAM dependent methyltransferases. SAM is the classical methyl donor for methyltrasferases, however, examples of other methyl donors are seen in nature. The general mechanism for methyl transfer is a SN2-like nucleophilic attack where the methionine sulfur serves as the leaving group and the methyl group attached to it acts as the electrophile that transfers the methyl group to the enzyme substrate. SAM is converted to S-Adenosyl homocysteine (SAH) during this process. The breaking of the SAM-methyl bond and the formation of the substrate-methyl bond happen nearly simultaneously. These enzymatic reactions are found in many pathways and are implicated in genetic diseases, cancer, and metabolic diseases. Another type of methyl transfer is the radical S-Adenosyl methionine (SAM) which is the methylation of unactivated carbon atoms in primary metabolites, proteins, lipids, and RNA.

Trestolone

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.

5-Methyl-MDA

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

Selfotel

Selfotel (CGS-19755) is a drug which acts as a competitive NMDA antagonist, directly competing with glutamate for binding to the receptor. Initial studies showed it to have anticonvulsant, anxiolytic, analgesic and neuroprotective effects, and it was originally researched for the treatment of stroke, but subsequent animal and human studies showed phencyclidine-like effects, as well as limited efficacy and evidence for possible neurotoxicity under some conditions, and so clinical development was ultimately discontinued.

MDMAI

5,6-Methylenedioxy-N-methyl-2-aminoindane (MDMAI), is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a putative entactogen in humans.

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

2-Methyl-MDA

2-Methyl-3,4-methylenedioxyamphetamine (2-methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It acts as a selective serotonin releasing agent (SSRA), with IC50 values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux. 2-Methyl-MDA is more potent than MDA and 5-methyl-MDA. However, it is slightly more selective for serotonin over dopamine and norepinephrine release in comparison to 5-methyl-MDA.

6-Methyl-MDA

6-Methyl-3,4-methylenedioxyamphetamine (6-Methyl-MDA) is an entactogen and psychedelic drug of the amphetamine class. It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).

LY-235959

LY-235959 is a competitive antagonist at the NMDA receptor. It has analgesic and neuroprotective effects and causes hypothermia in animal models, as well as reducing the development of tolerance to morphine and altering the reinforcing effects of cocaine.

4-Methylphenethylamine Chemical compound

4-Methylphenethylamine (4MPEA), also known as para-methylphenethylamine, is an organic compound with the chemical formula of C9H13N. 4MPEA is a human trace amine associated receptor 1 (TAAR1) agonist, a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine. 4MPEA also appears to inhibit the human cytochrome P450 enzymes CYP1A2 and CYP2A6, based upon the published literature.

PD-137889 Chemical compound

PD-137889 (N-methylhexahydrofluorenamine) is a chemical compound that is active as an NMDA receptor antagonist in the central nervous system at roughly 30 times the potency of the "flagship" of its class, ketamine, and substitutes for phencyclidine in animal studies. Ki [3H]TCP binding = 27 nM versus ketamine's Ki = 860 nM.

References

  1. Bulay O, Mirvish SS (September 1979). "Carcinogenesis in rat esophagus by intraperitoneal injection of different doses of methyl-n-amylnitrosamine". Cancer Res. 39 (9): 3644–6. PMID   476689.