Nornicotine

148.21

148.21

83H6L5QD8Z

DTXSID7075420

Hygroscopic, somewhat viscous liquid

2933990090

24.9

0.2

1.044 g/cm³ @ Temp: 19 °C

270 °C

111.291ºC

1.536

Miscible in water; Very soluble in alcohol, chloroform, ether, petr ether, kerosene, oils

Refrigerator, under inert atmosphere

0.00923 mm Hg at 25 deg C (est)

LDLo ipr-rat: 23,500 mg/kg MEIEDD 10,963,83

Specific optical rotation: -89 degrees at 22 °C

Develops a slight amine odor, less pungent than that of nicotine

Henry's Law constant = 1.37X10-9 atm-cu m/mol at 25 °C (est)

pKa = 5.25 (est)

Hardly volatile with steam|More stable than nicotine, not darkening on exposure to light and air|Hydroxyl radical reaction rate constant = 8.67X10-11 cu cm/molecule-sec at 25 °C (est)

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

The concentration of nornicotine in environmental tobacco smoke has been reported as 1.0 umol/mol carbon monoxide(1).

... Nornicotine causes aberrant protein glycation and catalyzes the covalent modification of certain prescription drugs such as the commonly used steroid, prednisone. ...

LD50 Mouse intravenous 3409 ug/kg (3.409 mg/kg)|LD50 Mouse intraperitoneal 14,660 ug/kg (14.66 mg/kg)|LD50 Rabbit intravenous 3 mg/kg

Nornicotine occurs in tobacco (Nicotiana Tabacum), other species of Nicotiana, and indigenous Australian plants such as Duboisia Hopwoodii and Duboisia Myoporoides(1-3); all these plants are members of the Solanacae family(2,3). Nornicotine has been identified as a chemical component in tobacco(4).

Nornicotine has been identified as a chemical component in tobacco smoke and in substituent tobacco smoke(1). Nornicotine's former production and use as an insecticide(2) may have resulted in its direct release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), estimated Koc values of 500 and 14(SRC), determined respectively from a structure estimation method(2) and using a log Kow of 0.17(3) and a regression-derived equation(2), indicates that nornicotine may have very high to moderate mobility in soil(SRC). The estimated pKa of nornicotine is 5.25(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of nornicotine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.37X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Nornicotine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.00923 mm Hg at 25 °C(SRC), determined from a fragment constant method(2).|AQUATIC FATE: Based on a classification scheme(1), estimated Koc values of 500 and 14(SRC), determined respectively from a structure estimation method(2) and using a log Kow of 0.17(3) and a regression-derived equation(2), indicates that nornicotine may have no to moderate adsorption to suspended solids and sediment(SRC). The estimated pKa of nornicotine is 5.25(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5); therefore, moderate adsorption may be more likely to occur with the cation form(SRC). Volatilization from water surfaces is not expected(6) based upon an estimated Henry's Law constant of 1.37X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(7), an estimated BCF of 3(SRC), from its log Kow of 0.17(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Nornicotine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nornicotine, which has an estimated vapor pressure of 0.00923 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nornicotine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.4 hours(SRC), calculated from its rate constant of 8.67X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Nornicotine does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of nornicotine with photochemically-produced hydroxyl radicals has been estimated as 8.67X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Nornicotine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Nornicotine does not contain chromophores that absorb at wavelengths >290 nm(2) and it is reported to not darkened on exposure to light(3); therefore it is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for nornicotine(SRC), using a log Kow of 0.17(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of nornicotine is estimated as 14(SRC), using a log Kow of 0.17(1) and a regression-derived equation(2). Using a structure estimation method based on molecular connectivity indices(2), the Koc can be estimated to be 500(SRC). According to a classification scheme(3), these estimated Koc value suggest that nornicotine may have very high to moderate mobility in soil. The estimated pKa of nornicotine is 5.25(4), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for nornicotine is estimated as 1.37X10-9 atm-cu m/mole at 25 °C(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that nornicotine is expected to be essentially nonvolatile water surfaces(2). Nornicotine's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). Nornicotine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.00923 mm Hg at 25 °C(SRC), determined from a fragment constant method(1).

Nornicotine's occurrence in tobacco and tobacco smoke will expose the general population to nornicotine through inhalation of tobacco smoke and through dermal contact with tobacco leaves and tobacco products. (SRC)

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Nornicotine is a known human metabolite of nicotine.

/CASE REPORTS/ Umbilical cord tissue was studied as a means of detecting prenatal exposure to nicotine. ... Between June and September 2009, 19 women with a tobacco exposure history (either first- or second-hand tobacco smoke exposure during pregnancy) were consented for the study. A questionnaire was completed to document nicotine exposure during each trimester of pregnancy. All infants were delivered at term (38 weeks or greater) and paired umbilical cord tissue (10-cm segment or greater) and meconium were obtained. ... Nornicotine was detected only in meconium, at very low concentrations. ... All analyte concentrations were lowest when the mother stated she quit smoking early in pregnancy or had only second-hand exposure, and detection was poor if exposure was limited to the first or second trimesters. ...

3-(2-pyrrolidinyl)pyridine