pilocarpine
2(3H)-furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S-cis)-
Identification
| Name | pilocarpine |
| IUPAC | (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one |
| CAS Number | 92-13-7 |
| EINECS | 202-128-4 |
| FDA UNII | 01MI4Q9DI3 |
| Molecular Formula | C11 H16 N2 O2 |
| Molecular Weight | 208.26092000 |
| Nikkaji Number | J9.328I |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 34.00 °C. @ 760.00 mm Hg |
| Boiling Point | 431.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 419.00 °F. TCC ( 215.00 °C. ) (est) |
| logP (o/w) | 0.120 |
| Soluble in | water, 3.133e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | unreported-man LDLo 1912 ug/kg |
| Dermal Toxicity | subcutaneous-human LDLo 143 ug/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: COMA\nLUNGS, THORAX, OR RESPIRATION: CYANOSIS\nVASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for pilocarpine usage levels up to | not for fragrance use. |
| Recommendation for pilocarpine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(3S,4R)-3-
ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one
2(3H)-
furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, (3S-cis)-
imidazole-5-butyric acid, alpha-ethyl-beta-(hydroxymethyl)-1-methyl-, gamma-lactone
ocusert P 20
ocusert pilo
ocusert pilo-20
ocusert pilo-40
pilocarpin
pilocarpol
pilokarpin
pilokarpol
syncarpine
PubMed:
Activation of brain indoleamine 2,3-dioxygenase contributes to epilepsy-associated depressive-like behavior in rats with chronic temporal lobe epilepsy.
PubMed:
Speed modulation of hippocampal theta frequency correlates with spatial memory performance.
PubMed:
Nucleus accumbens neurotransmission and effort-related choice behavior in food motivation: effects of drugs acting on dopamine, adenosine, and muscarinic acetylcholine receptors.
PubMed:
E2f1-deficient NOD/SCID mice have dry mouth due to a change of acinar/duct structure and the down-regulation of AQP5 in the salivary gland.
PubMed:
Functional and proteomic analysis of submandibular saliva in rats exposed to chronic stress by immobilization or constant light.
PubMed:
Salivary 8-OHdG Induction by Physical Exercise Training Under Food Restriction.
PubMed:
Salivary secretions from the honeybee mite, Varroa destructor: effects on insect haemocytes and preliminary biochemical characterization.
PubMed:
Metabolic alterations in different developmental stages of Pilocarpus microphyllus.
PubMed:
Attenuation of cocaine's reinforcing and discriminative stimulus effects via muscarinic M1 acetylcholine receptor stimulation.
PubMed:
Availability of saliva for the assessment of alterations in the autonomic nervous system caused by physical exercise training.
PubMed:
The effects of pilocarpine-induced status epilepticus on oxidative stress/damage in developing animals.
PubMed:
Insidious weight gain in prepubertal seized rats treated with an atypical neuroleptic: the role of food consumption, fluid consumption, and spontaneous ambulatory activity.
PubMed:
[Zinc and insulin level in islet cells under various functional state of insular apparatus].
PubMed:
Food for thought: honeybee foraging, memory, and acetylcholine.
PubMed:
[Xerostomia in palliative care].
PubMed:
Herbal treatment following post-seizure induction in rat by lithium pilocarpine: Scutellaria lateriflora (Skullcap), Gelsemium sempervirens (Gelsemium) and Datura stramonium (Jimson Weed) may prevent development of spontaneous seizures.
PubMed:
Effect of food deprivation during early development on cognition and neurogenesis in the rat.
PubMed:
M(3) muscarinic acetylcholine receptor plays a critical role in parasympathetic control of salivation in mice.
PubMed:
Hippocampal N-acetyl aspartate levels do not mirror neuronal cell densities in creatine-supplemented epileptic rats.
PubMed:
Neuroendocrine alterations impair enamel mineralization, tooth eruption and saliva in rats.
PubMed:
Regulation of muscarinic acetylcholine receptor function in acetylcholinesterase knockout mice.
PubMed:
Increased drinking in mutant mice with truncated M5 muscarinic receptor genes.
PubMed:
Seizure onset times for rats receiving systemic lithium and pilocarpine: sources of variability.
PubMed:
Weight gain in post-seized rats is facilitated by adding aspirin, glucose, or glucose-taurine-acetaminophen to food mush.
PubMed:
Changes of salivary amylase in serum and parotid gland during pharmacological and physiological stimulation.
PubMed:
Brief successive temporal observational sampling as a possible indicator of daily overt seizure activity in epileptic rats.
PubMed:
Synchronized feeding as a "conditioned stimulus" for overt seizures in chronically (limbic) epileptic rats: a model for "psychogenic seizures" with complex partial epilepsy.
PubMed:
Post-radiation severe xerostomia relieved by pilocarpine: a prospective French cooperative study.
PubMed:
Update in Sjögren syndrome.
PubMed:
Disorder of salivary secretion in inbred polydipsic mouse.
PubMed:
Fetal alcohol-exposed rats exhibit differential response to cholinergic drugs on a delay-dependent memory task.
PubMed:
Defective secretion of saliva in transgenic mice lacking aquaporin-5 water channels.
PubMed:
Preemptive pharmacologic intervention in radiation-induced salivary dysfunction.
PubMed:
Vascular protein leakage in the rat parotid gland elicited by reflex stimulation, parasympathetic nerve stimulation and administration of neuropeptides.
PubMed:
Transient tonic pupils in botulism type B.
PubMed:
Detection of visual signals by rats: effects of chlordiazepoxide and cholinergic and adrenergic drugs on sustained attention.
PubMed:
Fluoride and pilocarpine reduce the risk of caries produced by chronic clomipramine treatment in rats.
PubMed:
Comments on the pathogenesis of muscarinic agonist-induced corneal opacities in rats.
PubMed:
Cytotoxicity in chicken alimentary secretions as measured by a derivative of the tumor necrosis factor assay.
PubMed:
First effective drug for dry mouth.
PubMed:
Oral pilocarpine (Salagen)--a recently approved salivary stimulant.
PubMed:
Visoltricin, a novel biologically active compound produced by Fusarium tricinctum.
PubMed:
Pharmacological characterization of performance on a concurrent lever pressing/feeding choice procedure: effects of dopamine antagonist, cholinomimetic, sedative and stimulant drugs.
PubMed:
Pancreatic B-cell culture after intravitam B-cell selection with nitric pilocarpine and modified B-technique use.
PubMed:
Transient blocking of persistent gnawing by haloperidol in rats with seizure-induced multifocal brain damage.
PubMed:
Attenuation of scopolamine-induced spatial memory deficits in the rat by cholinomimetic and non-cholinomimetic drugs using a novel task in the 12-arm radial maze.
PubMed:
Interactions between scopolamine and muscarinic cholinergic agonists or cholinesterase inhibitors on spatial alternation performance in rats.
PubMed:
Functional morphology of accommodation in the raccoon.
PubMed:
A study of stimuli operative in the release of antibodies in the rat intestine.
PubMed:
Salivatory neurons in the brainstem nucleus parvocellularis of the rat: effects of electrolytic lesions.
PubMed:
Discriminative stimulus properties of physostigmine in rats.
PubMed:
Discriminative stimulus properties of muscarinic agonists.
PubMed:
Deaths of two hospital inpatients poisoned by pilocarpine.
PubMed:
Effects of muscarinic receptor antagonism upon two forms of stress-induced analgesia.
PubMed:
Cholinergic suppression: a postsynaptic mechanism of long-term associative learning.
PubMed:
[Effect of the intake of food and of biologically active substances on the capacity of the blood serum to inhibit proteolytic activity].
PubMed:
Pilocarpine and physostigmine attenuate spatial memory impairments produced by lesions of the nucleus basalis magnocellularis.
PubMed:
Stability of pilocarpine hydrochloride and pilocarpine nitrate ophthalmic solutions submitted by U.S. hospitals.
PubMed:
[Xerostomia. II. Therapeutic possibilities].
PubMed:
Disordered drinking in developing spontaneously hypertensive rats.
PubMed:
Effect of chronic administration of deoxycorticosterone acetate on salt appetite of captopril-treated rats.
PubMed:
Trigger activation of the paradoxical salivatory response to atropine in the parasympathetically denervated human parotid gland.
PubMed:
Radioprotection by WR-2721 of gamma-irradiated rat parotid gland: effect on gland weight and secretion at 8-10 days post irradiation.
PubMed:
Clinical implications of reported timolol-induced side effects.
PubMed:
Growth, appetite, sequence of pathological signs and survival following the induction of rapid, synchronous vitamin A deficiency in the rat.
PubMed:
Immediate transformation of the cholinonegative effect of atropine into a cholinopositive one in denervated human salivary gland by reflex stimulations.
PubMed:
[Decrease of ACh response in isolated duodenum from SART stressed (repeated cold stressed) mice (author's transl)].
PubMed:
Trialwise tracking method for measuring drug-affected sensory threshold changes in animals.
PubMed:
Pilocarpine, food deprivation, and induction of mouse killing by cats.
PubMed:
Effects of combining pilocarpine, d-amphetamine, and either a free feeding schedule or cyclic food deprivation on mouse killing by rats.
PubMed:
Rate of protein synthesis in rat salivary gland cells after pilocarpine or feeding. II. Protein synthesis in vivo in cells of the submandibular and parotid gland after secretion.
PubMed:
Rate of protein synthesis in rat salivary gland cells after pilocarpine or feeding. I. Rate of (glyco) protein secretion from cells of mixed salivary glands.
PubMed:
Metiamide: an antagonist of histamine-stimulated gastric acid secretion.
PubMed:
Effects of fasting and feeding and pilocarpine on paneth cells of the mouse.
PubMed:
The effects of secretagogues on the incorporation of (2- 3 H)myoinositol into lipid in cytological fractions in the pancreas of the guinea pig in vivo.
PubMed:
Amylase and other protein components of parotid saliva of the baboon, Papio anubis.
PubMed:
Renin-like activity of the rat submaxillary gland: characterization and the effect of several drugs and stimuli.
PubMed:
[Innervation of the dog submandibular gland].
PubMed:
Protein synthesis in the pancreas of the rat after stimulation of secretion.