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arecaidine
isoguvacine

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Name:1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
CAS Number: 499-04-7Picture of molecule3D/inchi
FDA UNII: 0S8YEV0D4O
Nikkaji Web:J6.114J
Beilstein Number:0112366
MDL:MFCD00985225
XlogP3:-2.30 (est)
Molecular Weight:141.17007000
Formula:C7 H11 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 232.00 °C. @ 760.00 mm Hg
Boiling Point: 266.70 °C. @ 760.00 mm Hg (est)
Flash Point: 239.00 °F. TCC ( 115.10 °C. ) (est)
logP (o/w): 0.770 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Arecaidine >95%
Odor: characteristic
Use: Arecaidine is found in the fruits of Areca catechu, it has tumorgenicity.
Carbosynth
For experimental / research use only.
Arecaidine
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for arecaidine usage levels up to:
 not for fragrance use.
 
Recommendation for arecaidine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10355
National Institute of Allergy and Infectious Diseases:Data
1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
Chemidplus:0000499047
 
References:
 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):10355
Pubchem (sid):134977777
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10128
HMDB (The Human Metabolome Database):HMDB30352
FooDB:FDB002197
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 areca catechu seed
Search Trop Picture
 
Synonyms:
 arecaine
isoguvacine
 methyl guvacine
1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid
1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid
1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid
 methylguvacine
N-methylguvacine
 nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-
3-pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-
3-pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl- (9CI)
1,2,5,6-tetrahydro-1-methyl nicotinic acid
1,2,5,6-tetrahydro-1-methyl-3-pyridine carboxylic acid
1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxylic acid
1,2,5,6-tetrahydro-1-methylnicotinic acid
 

Articles:

PubMed:Betel chewing and arecoline affects eotaxin-1, asthma and lung function.
PubMed:M2 muscarinic receptor activation regulates Schwann cell differentiation and myelin organization.
PubMed:M2 receptors exert analgesic action on DRG sensory neurons by negatively modulating VR1 activity.
PubMed:Effects of muscarinic agents on chick choroids in intact eyes and eyecups: evidence for a muscarinic mechanism in choroidal thinning.
PubMed:M2 receptor activation inhibits cell cycle progression and survival in human glioblastoma cells.
PubMed:Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1).
PubMed:The effect of indomethacin on the muscarinic induced contractions in the isolated normal guinea pig urinary bladder.
PubMed:Areca nut-induced buccal mucosa fibroblast contraction and its signaling: a potential role in oral submucous fibrosis--a precancer condition.
PubMed:Activation of TGF-β pathway by areca nut constituents: a possible cause of oral submucous fibrosis.
PubMed:Characterization of protein adducts formed by toxic alkaloids by nano-scale liquid chromatography with mass spectrometry.
PubMed:M2 muscarinic receptors inhibit cell proliferation in human glioblastoma cell lines.
PubMed:Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro.
PubMed:Interactions between cholinergic and prostaglandin signaling elements in the urothelium: role for muscarinic type 2 receptors.
PubMed:Potential action of betel alkaloids on positive and negative symptoms of schizophrenia: a review.
PubMed:High-throughput simultaneous analysis of five urinary metabolites of areca nut and tobacco alkaloids by isotope-dilution liquid chromatography-tandem mass spectrometry with on-line solid-phase extraction.
PubMed:Quantification of blood betel quid alkaloids and urinary 8-hydroxydeoxyguanosine in humans and their association with betel chewing habits.
PubMed:M(1)-like muscarinic acetylcholine receptors regulate fast-spiking interneuron excitability in rat dentate gyrus.
PubMed:Xenobiotic metabolism: a view through the metabolometer.
PubMed:Striatal muscarinic receptors promote activity dependence of dopamine transmission via distinct receptor subtypes on cholinergic interneurons in ventral versus dorsal striatum.
PubMed:A new matrix for analyzing low molecular mass compounds and its application for determination of carcinogenic areca alkaloids by matrix-assisted laser desorption ionization time-of-flight mass spectrometry.
PubMed:Mucosal muscarinic receptors enhance bladder activity in cats with feline interstitial cystitis.
PubMed:Volume-induced responses in the isolated bladder: evidence for excitatory and inhibitory elements.
PubMed:Role of hyperglycaemia in the pathogenesis of hypotension observed in type-1 diabetic rats.
PubMed:Acetylcholine inhibits cell cycle progression in rat Schwann cells by activation of the M2 receptor subtype.
PubMed:Increase of cardiac M2-muscarinic receptor gene expression in type-1 but not in type-2 diabetic rats.
PubMed:Urotheliogenic modulation of intrinsic activity in spinal cord-transected rat bladders: role of mucosal muscarinic receptors.
PubMed:Maturation of stretch-induced contractile activity and its muscarinic regulation in isolated whole bladder strips from rat.
PubMed:Damage to the bladder neck alters autonomous activity and its sensitivity to cholinergic agonists.
PubMed:A spinal muscarinic M2 receptor-GABAergic disinhibition pathway that modulates peripheral inflammation in mice.
PubMed:Cholinergic activation of phasic activity in the isolated bladder: possible evidence for M3- and M2-dependent components of a motor/sensory system.
PubMed:Muscarinic M1 acetylcholine receptors regulate the non-quantal release of acetylcholine in the rat neuromuscular junction via NO-dependent mechanism.
PubMed:The metabolomics of (+/-)-arecoline 1-oxide in the mouse and its formation by human flavin-containing monooxygenases.
PubMed:Interstitial cells and phasic activity in the isolated mouse bladder.
PubMed:Muscarinic stimulation of the rat isolated whole bladder: pathophysiological models of detrusor overactivity.
PubMed:Muscarinic stimulation of the mouse isolated whole bladder: physiological responses in young and ageing mice.
PubMed:Comparison study of autonomous activity in bladders from normal and paraplegic rats.
PubMed:A metabolomic approach to the metabolism of the areca nut alkaloids arecoline and arecaidine in the mouse.
PubMed:Genetic damage in cultured human keratinocytes stressed by long-term exposure to areca nut extracts.
PubMed:Bladder volume alters cholinergic responses of the isolated whole mouse bladder.
PubMed:Human vaginal mucosa as a model of buccal mucosa for in vitro permeability studies: an overview.
PubMed:The novel imidazopyridine 2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric-oxide synthase.
PubMed:Activation of muscarinic K+ channels by arecaidine propargyl ester in isolated guinea-pig atrial myocytes.
PubMed:Volume-induced effects on the isolated bladder: a possible local reflex.
PubMed:Cholinergic regulation of the evoked quantal release at frog neuromuscular junction.
PubMed:Activation of muscarinic acetylcholine receptors elicits pigment granule dispersion in retinal pigment epithelium isolated from bluegill.
PubMed:Phosphodiesterase-linked inhibition of nonmicturition activity in the isolated bladder.
PubMed:High-performance liquid chromatographic determination of arecoline in human saliva.
PubMed:Modulation of autonomous contractile activity in the isolated whole bladder of the guinea pig.
PubMed:Cholinergic modulation of nociceptive responses in vivo and neuropeptide release in vitro at the level of the primary sensory neuron.
PubMed:Eosinophil-induced release of acetylcholine from differentiated cholinergic nerve cells.
PubMed:Augmented mRNA expression of tissue inhibitor of metalloproteinase-1 in buccal mucosal fibroblasts by arecoline and safrole as a possible pathogenesis for oral submucous fibrosis.
PubMed:Comparative in vitro permeability of human vaginal, small intestinal and colonic mucosa.
PubMed:Agonist- and nerve-induced phasic activity in the isolated whole bladder of the guinea pig: evidence for two types of bladder activity.
PubMed:Electrophysiological characterization of cardiac muscarinic acetylcholine receptors: different subtypes mediate different potassium currents.
PubMed:Autonomous activity in the isolated guinea pig bladder.
PubMed:The relationship between areca nut usage and heart rate in lactating Bangladeshis.
PubMed:Effects of Ba-Wei-Die-Huang-Wan on the cholinergic function and protein expression of M2 muscarinic receptor of the urinary bladder in diabetic rats.
PubMed:[Pharmacological parameters of muscarinic cholinoreceptors in skeletal muscles].
PubMed:Presynaptic muscarinic M(2)-receptor-mediated inhibition of N-type Ca(2+) channels in cultured sphenopalatine ganglion: direct evidence for acetylcholine inhibition of cerebral nitrergic neurogenic vasodilation.
PubMed:Permeability of human intestinal mucosa using a continuous flow-through perfusion system.
PubMed:Areca nut extract lowers the permeability of vaginal mucosa to reduced arecoline and arecaidine.
PubMed:Muscarinic M2 receptors inhibit heat-induced CGRP release from isolated rat skin.
PubMed:The effects of arecoline on the release of cytokines using cultured peripheral blood mononuclear cells from patients with oral mucous diseases.
PubMed:Role of areca nut in betel quid-associated chemical carcinogenesis: current awareness and future perspectives.
PubMed:Effects of Betel chewing on the central and autonomic nervous systems.
PubMed:Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin.
PubMed:Diffusion of reduced arecoline and arecaidine through human vaginal and buccal mucosa.
PubMed:Dual effects of muscarinic M(2) acetylcholine receptors on the synthesis of cyclic AMP in CHO cells: dependence on time, receptor density and receptor agonists.
PubMed:Cancer induction in the DMBA hamster cheek pouch: a modified technique using a promoter.
PubMed:Carbachol and acetylcholine delay the early postdenervation depolarization of muscle fibres through M1-cholinergic receptors.
PubMed:Muscarinic properties of compounds related to arecaidine propargyl ester.
PubMed:Behavioral and biochemical studies of dichloromethane fraction from the Areca catechu nut.
PubMed:Neuronal soma-dendritic and prejunctional M1-M4 receptors in gastrointestinal and genitourinary smooth muscle.
PubMed:Deficiency in collagen and fibronectin phagocytosis by human buccal mucosa fibroblasts in vitro as a possible mechanism for oral submucous fibrosis.
PubMed:Mechanism of prejunctional muscarinic receptor-mediated inhibition of neurogenic vasodilation in cerebral arteries.
PubMed:Muscarinic facilitation of GABA release in substantia gelatinosa of the rat spinal dorsal horn.
PubMed:M2 receptor binding of the selective antagonist AF-DX 384: possible involvement of the common allosteric site.
PubMed:Characterization of postjunctional muscarinic receptors mediating contraction in rat anococcygeus muscle.
PubMed:Contraction of guinea-pig gallbladder: muscarinic M3 or M4 receptors?
PubMed:Quantitative colorimetric and gas chromatographic determination of arecaidine propargyl ester.
PubMed:Inflammatory modulation of muscarinic receptor activation in canine ileal circular muscle cells.
PubMed:Acetylcholine-induced vasoconstrictor response of coronary vessels in rats: a possible contribution of M2 muscarinic receptor activation.
PubMed:Modulation of noradrenaline release from isolated human atrial appendages.
PubMed:The mutagenicities of alkaloids and N-nitrosoguvacoline from betel quid.
PubMed:Minimal arecaidine concentrations showing a promotion effect during DMBA-induced hamster cheek pouch carcinogenesis.
PubMed:Regulation of mucous acinar exocrine secretion with age.
PubMed:In vitro production of interleukin-6 by human gingival, normal buccal mucosa, and oral submucous fibrosis fibroblasts treated with betel-nut alkaloids.
PubMed:Aliphatic and heterocyclic analogues of arecaidine propargyl ester. Structure-activity relationships of mono- and bivalent ligands at muscarinic M1 (M4), M2 and M3 receptor subtypes.
PubMed:Functional characterization of a muscarinic receptor stimulating gastrin release from rabbit antral G-cells in primary culture.
PubMed:Observations on the effect of areca nut extracts on oral fibroblast proliferation.
PubMed:Involvement of gamma-aminobutyric acid in the stimulatory effect of metoclopramide on gastrointestinal motility.
PubMed:Characterization of the prejunctional muscarinic receptors mediating inhibition of evoked release of endogenous noradrenaline in rabbit isolated vas deferens.
PubMed:Characterization of muscarinic receptors mediating vasodilation in rat perfused kidney.
PubMed:Characterization of muscarinic receptors in rat kidney.
PubMed:Cholinergic agents: effect of methyl substitution in a series of arecoline derivatives on binding to muscarinic acetylcholine receptors.
PubMed:Characterization of muscarinic receptors mediating vasodilation in guinea-pig ileum submucosal arterioles by the use of computer-assisted videomicroscopy.
PubMed:Role of muscarinic receptor subtypes in central antinociception.
PubMed:Effect of extracellular calcium concentration on potency of muscarinic agonists at M1 and M2 receptors in rabbit vas deferens.
PubMed:Pharmacology of the putative M4 muscarinic receptor mediating Ca-current inhibition in neuroblastoma x glioma hybrid (NG 108-15) cells.
PubMed:Pharmacological characterization of the vascular muscarinic receptors mediating relaxation and contraction in rabbit aorta.
PubMed:Different effects of muscarinic agonists in rat superior cervical ganglion and hippocampal slices.
PubMed:Muscarinic receptor-mediated prostacyclin and cGMP synthesis in cultured vascular cells.
PubMed:Central effects of muscarinic agonists and antagonists on hippocampal theta rhythm and blood pressure in the anaesthetised rat.
PubMed:Methoctramine, a cardioselective antagonist: muscarinic receptor mediating prostaglandin synthesis in isolated rabbit heart.
PubMed:Areca-nut toxicity in cultured human buccal epithelial cells.
PubMed:Relative potencies of agonists and differential sensitivity to N-ethylmaleimide on muscarinic autoreceptors and postsynaptic receptors in rat hippocampus.
PubMed:Anti-insulin antiserum increases inositol phosphate accumulation in rat pancreatic islets.
PubMed:Muscarinic receptor subtypes in rat pancreatic islets: binding and functional studies.
PubMed:Prostacyclin synthesis elicited by cholinergic agonists is linked to activation of M2 alpha and M2 beta muscarinic receptors in the rabbit aorta.
PubMed:Binding characteristics of the muscarinic receptor subtype in rabbit pancreas.
PubMed:Cytotoxic and genotoxic effects of areca nut-related compounds in cultured human buccal epithelial cells.
PubMed:Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester.
PubMed:AF-DX 116 differentiates between prejunctional muscarine receptors located on noradrenergic and cholinergic nerves.
PubMed:Structure-activity relationships of new analogues of arecaidine propargyl ester at muscarinic M1 and M2 receptor subtypes.
PubMed:Muscarinic stimulation of prostanoid synthesis by the isolated rat trachea: calcium dependency and effect of cortisol and cigarette smoke.
PubMed:Effect of M2 muscarinic receptor antagonist 4-DAMP, on prostaglandin synthesis and mechanical function in the isolated rabbit heart.
PubMed:The relative potencies of cholinomimetics and muscarinic antagonists on the rat iris in vivo: effects of pH on potency of pirenzepine and telenzepine.
PubMed:Contribution of M2 alpha and M2 beta muscarinic receptors to the action of cholinergic stimuli on prostaglandin synthesis and mechanical function in the isolated rabbit heart.
PubMed:Prostaglandin synthesis elicited by cholinergic stimuli is mediated by activation of M2 muscarinic receptors in rabbit heart.
PubMed:Stimulation of human fibroblast collagen synthesis in vitro by gamma-aminobutyric acid.
PubMed:Competitive and non-competitive antagonism exhibited by 'selective' antagonists at atrial and ileal muscarinic receptor subtypes.
PubMed:[The spasmolytic activity of propiverine and some of its structural analogs].
PubMed:Stimulation of ganglionic muscarinic M1 receptors by a series of tertiary arecaidine and isoarecaidine esters in the pithed rat.
PubMed:An in-vitro comparison of human fibroblasts from normal and oral submucous fibrosis tissue.
PubMed:Effects of arecaidine application to hamster cheek pouch.
PubMed:The selectivity of the (-)-and (+)-forms of hyoscine methiodide and of hyoscyamine camphorsulphonate for muscarinic (M2) receptors.
PubMed:Effects of arecaidine application to hamster cheek pouch.
PubMed:Uptake of gamma-aminobutyric acid and glycine by synaptosomes from postmortem human brain.
PubMed:Interaction of some muscarinic agonists and antagonists at the prejunctional muscarinic receptor in the rabbit ear artery preparation.
PubMed:Stimulation of human buccal mucosa fibroblasts in vitro by betel-nut alkaloids.
PubMed:The relative potencies of some agonists at M2 muscarinic receptors in guinea-pig ileum, atria and bronchi.
PubMed:Induction of in vivo sister chromatid exchanges by arecaidine, a betel nut alkaloid, in mouse bone-marrow cells.
PubMed:Hydrolysis of ester- and amide-type drugs by the purified isoenzymes of nonspecific carboxylesterase from rat liver.
PubMed:Mutagenicity of betel quid and its ingredients using mammalian test systems.
PubMed:[Structure- and conformation-activity relationships of heterocyclic acetylcholine analogs, 18. Synthesis and muscarine-type activity of sulfoarecaidine and sulfoisoarecaidine esters].
PubMed:[Structure- and conformation-activity relationships of heterocyclic acetylcholine analogs. 17. Conformational behavior and cholinergic properties of arecaidine and sulfoarecaidine esters].
PubMed:Correlation of mutagenicity and tumorigenicity of betel quid and its ingredients.
PubMed:[Structure- and conformation-activity relationships of heterocyclic acetylcholine analogues. 16. Conformational behaviour and cholinergic properties of isoarecaidine and sulfoisoarecaidine esters].
PubMed:Muscarinic effects of various isoarecaidine esters in sympathetic ganglia.
PubMed:Betel nuts, arecaidine, and oral cancer.
PubMed:Arecaidine and schizophrenia.
PubMed:The central action of various arecaidine esters (arecoline derivatives) on blood pressure and heart rate in the cat. Comparison with the peripheral effects.
PubMed:Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system.
PubMed:Central action of some cholinergic drugs (arecaidine esters) and nicotine on blood pressure and heart rate of cats.
PubMed:[Structure-activity relationships of unsaturated esters of arecaidine and dihydroarecaidine].
PubMed:Studies on arecaidine and quinuclidine derivatives--discovery of a sigmatropic rearrangement in the 2-dehydroquinuclidine system.
PubMed:The metabolic interconversion of arecoline and arecoline 1-oxide in the rat.
PubMed:[Pharmacology of the active substances in betel. 3. Experiments with arecaidine].
PubMed:Mercapturic acid formation during the metabolism of arecoline and arecaidine in the rat.
PubMed:Some derivatives of arecaidine.
PubMed:[Use of 14C-labelled arecaidine esters to estimate the number of acetylcholine receptors in muscle tissue].
PubMed:["Receptor-binding" of 14C-arecaidine derivatives by atrial tissue, as influenced by pH, atropine and membrane depolarization].
PubMed:Estimation of the cholinergic receptor occupation in guinea pig isolated atria by means of 14C-labelled arecaidine-derivatives.
PubMed:Occupation of the cholinergic receptors in smooth muscle estimated with the aid of 14C-labelled arecaidine-derivatives.
PubMed:[On the pharmacology of active materials from betel. 2. Transformation of arecoline to arecaidine].
PubMed:[Electron distribution and dissociation constants of pharmacologically active Arecaidine derivatives].
PubMed:Investigations on structure-activity relationships of arecaidine-derivatives on the guinea pig isolated atria.
PubMed:[On the effect of arecaidine derivatives on the chronically denervated rat diaphragm].
PubMed:[On the affinity of arecaidine derivatives for acetylcholinesterase of guinea pig erythrocytes].
PubMed:The action of tertiary and quaternary arecaidine and dihydroarecaidine esters on the guinea pig isolated ileum.
PubMed:[On the effect of arecaidine esters on the blood pressure of the cat].
PubMed:Dissociation constants of some compounds related to lysergic acid. II. Ergometrine, ergometrinine and alkanolamides of 3-dimethylaminopropionic acid, 1-methylhexahydronicotinic acid and arecaidine.
PubMed:[Effect on the central nervous system of simplified structural analogs of LSD 25 derived from arecaidine amides].
 
Notes:
Alkaloid from nuts of Areca catechu (betel nuts)
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