Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13N3O2 |
| Molecular Weight | 207.2291 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(CCCC(=O)C1=CN=CC=C1)N=O
InChI
InChIKey=FLAQQSHRLBFIEZ-UHFFFAOYSA-N
InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
| Molecular Formula | C10H13N3O2 |
| Molecular Weight | 207.2291 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone or nicotine-derived nitrosamine ketone (NNK) is a tobacco-specific nitrosamine. NNK is considered to be a carcinogen. NNK induces deleterious mutations in oncogenes and tumor suppression genes by forming DNA adducts, which could be considered as tumor initiation. Meanwhile, the binding of NNK to the nicotinic acetylcholine receptor promotes tumor growth by enhancing and deregulating cell proliferation, survival, migration, and invasion, thereby creating a microenvironment for tumor growth.
Approval Year
Sample Use Guides
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) has been tested for carcinogenicity by various routes of administration in adult mice, rats, and Syrian hamsters, and in limited experiments in mink and ferrets.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:19:24 GMT 2023
by
admin
on
Fri Dec 15 17:19:24 GMT 2023
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| Record UNII |
7S395EDO61
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| Record Status |
Validated (UNII)
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NNK
Created by
admin on Fri Dec 15 17:19:24 GMT 2023 , Edited by admin on Fri Dec 15 17:19:24 GMT 2023
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| Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Highly effective lung carcinogen in rats and induces lung tumors in mice and hamsters as well (1) . It also causes tumors of the pancreas, liver, and nasal mucosa in rats. NNK (ng/cigarette)Canadian = 448.5 SD(237.4)Imported = 437.2 SD(376.1)
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE REACTIVE TYPE->PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE TOXIC -> PARENT | |||
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METABOLITE -> PARENT |
Pre-clinical
IN-VIVO
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE LESS ACTIVE -> PARENT |
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METABOLITE TOXIC -> PARENT |
Activated metabolite that leads to carcinogenesis.
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METABOLITE TOXIC -> PARENT |
Activated metabolite that leads to carcinogenesis
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![Structure of 4-[(Hydroxymethyl)nitrosoamino]-1-(3-pyridinyl)-1-butanone](/img/0b355da8-3b70-4dd2-a2f0-cd388699356d.svg "Structure of 4-[(Hydroxymethyl)nitrosoamino]-1-(3-pyridinyl)-1-butanone")
