Nicotine

Introduction to Nicotine

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Nicotine is an alkaloid present in Nicotiana Tabacum, a member of the Nightshade family.
The Nicotiana family is native to North and Soth America, Australasia and Western Africa, although are also grown ornamentally throughout the world.
The Nicotiana plant flowers in summer and can range from red to yellow.
Nicotiana Tabacum flowers are mid-pink in colour, and this is the sub-species most popularly used in cigarette and cigar tobacco production.
See separate wiki on tobacco here: http://www.drugs-forum.com/threads/99980

Nicotine, and the plant genus nicotiana are both named after the French Ambassador to Portugal, Jean Nicot.

Using Nicotine

Ways of administration

Nicotine is most commonly ingested via the smoking of tobacco in cigarettes, cigars or pipes.
Nicotine is also used via tobacco in snuff or Snus and chewing tobacco.
Nicotine is also available as patches (for smoking cessation), in tablets, inhalers, nasal spays, 'fake' cigarettes containing only nicotine... these work in a similar way to inhalers, sub-lingual microtabs, chewing gum and lozenges.
Nicotine can also be inhaled via the use of a vaporizer.

Effects of Nicotine

Nicotine in a non-smoker or one with no tolerance has a stimulant effect. However, to an addicted person or a person with some tolerance, the effect is more relaxing due to the nicotinic receptors in the brain being given their 'fix'.
Nicotine is an appetite suppressant, which is why many people who have quit nicotine use (usually by quitting smoking) have a tendency to gain weight.
Also, nicotine cravings in withdrawal are often mistaken for hunger, causing increased intake of food.

Combinations with Nicotine

Different Uses for Nicotine

Pharmacology of Nicotine

LD50 (mg/kg) (as the freebase) [1] :
Mice : 230 orally, 9.5 intraperitoneally, 0.3 intravenously

Nicotine affects nicotinic acetylcholine receptors. Acetylcholine is a neurotransmitter involved in memory, muscular movement, and autonomic functioning in both the sympathetic and parasympathetic nervous systems. Acetylcholine also affects muscarinic receptors, the receptors affected by muscaria mushrooms. Nicotine does not affect muscarinic receptors, and muscaria does not affect nicotinic receptors.

Effects on Gastric Emptying

Nicotine delays gastric empyting. Anything in the stomach stays in the stomach longer when nicotine is used. Since most drugs are absorbed more readily in the intestine, smoking may delay the onset of a drug. Some drugs (acidic drugs, such as aspirin) are absorbed more readily in the stomach. For such drugs nicotine may allow the drug to sit in the stomach longer, therefore increasing absorption.

Metabolic Induction

The cytochrome (cyp) P450 family of enzymes are involved in metabolizing a variety of drugs during Phase I metabolism. Metabolism of a drug generally deactivates that drug. When these enzymes are induced (or increased) there are more enzymes available to inactivate drugs. Nicotine induces specific cyp P450 enzymes, some of the key enzymes in drug metabolism. For drugs that are deactivated by these enzymes, nicotine use will decrease the duration of action. Certain drugs (called pro-drugs) must undergo metabolism in order to become active. For a pro-drug, nicotine use may help speed up the activation of the drug.

Chemistry of Nicotine

Column 1 Column 2
Systematic (IUPAC) name: (S)-3-(1-methyl-2-pyrrolidinyl)pyridine
Synonyms: 3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridine, 1-methyl-2-(3-pyridyl)pyrrolidine, ß-pyridyl-α-N-methylpyrrolidine, Habitrol, Nicabate, Nicoderm CQ, Nicolan, Nicopatch, Nicotinell, NiQuitin CQ, Tabazur; Nicotine neutral sulfate (sulfate); nicotine tartrate (tartrate); Eudermol (salicylate); Nicorette (polacrilex)
Molecular Formula: C10H14N2, C10H14N2.HCl (hydrochloride), C10H14N2.2[HCl] (dihydrochloride), [C10H14N2]2.H2SO4 (sulfate), C10H14N2.2[C4H6O6] (bitartrate), C10H16Cl4N2Zn.H2O (zinc chloride double salt monohydrate), C10H14N2.C7H6O3 (salicylate)
Molar mass: 162.24 g/mol, 198.69 g/mol (hydrochloride), 235.15 g/mol (dihydrochloride), 422.54 g/mol (sulfate), 462.41 g/mol (bitartrate), 389.45 g/mol (zinc chloride double salt monohydrate), 300.35 g/mol (salicylate) [2]
CAS Registry Number: 54-11-5, 2136-93-3 (hydrochloride), 6019-02-9 (dihydrochloride), 65-30-5 (sulfate), 65-31-6 (bitatrate), 29790-52-1 (salicylate), 96055-45-7 (polacrilex)
Melting Point: 90°C (bitartrate dihydrate), 118°C (salicylate)
Boiling Point: 123-125°C @ 17 mmHg, 247°C @ 745 mmHg (partial decomposition)
Flash Point: no data
Solubility: Freebase miscible with water (below 60°C); very soluble in alcohol, chloroform, ether, petroleum ether, kerosene, oils. Dihydrochloride very soluble in water, alcohol; nearly insoluble in ether. Sulfate soluble in water, alcohol. Bitartrate very soluble in water, alcohol. Zinc chloride double salt monohydrate very soluble in water; sparingly soluble in absolute alcohol and ether. Salicylate freely soluble in water, alcohol
Additionnal data: Freebase density 1.00925 (20°C); pK1 (15°C) 6.16, pK2 10.96; pH of 0.05M solution 10.2
Notes: Freebase aspect : colorless to pale yellow, oily liquid; very hygroscopic; turns brown on exposure to air or light; acrid burning taste; develops odor of pyridine; forms salts with almost any acid and double salts with many metals and acids. Hydrochloride aspect : deliquescent crystals; Dihydrochloride aspect : deliquescent crystals. Sulfate aspect : six-sided tablets; Bitartrate exists as the dihydrate form; Zinc chloride double salt monohydrate exists as the tetrahydrate; Salicylate aspect : six-sided plates
[1]

The dangers of Nicotine

Nicotine is absorbed throught the digestive tract, respiratory tract and throught skin. Death induced by nicotine results from paralysis of respiratory muscles.

Nicotine overdose is a rare but potentially fatal situation. Signs of nicotine overdose[1] include:
Abdominal cramps
Agitation, restlessness, or excitement
Muscular twitching
Breathing - rapid
Breathing - stops
Burning sensation in mouth
Coma
Confusion
Convulsions
Depression
Difficulty breathing
Drooling (increased salivation)
Fainting
Headache
Heartbeat - pounding and rapid, followed by slow heart rate
High blood pressure, which then drops
Vomiting
Weakness

In the event of nicotine overdose, medical attention must be sought as a matter of emergency.

The LD50 dosage for adults has been calculated at approximately 60mg. In children, the LD50 is considered approximately 10 mg.[2]

So, a small child chewing on a discarded nicotine patch could prove fatal.

Nicotine is a powerful toxin and must be treated with the same respect as any other drug.

The nicotine in one cigarette is enough to kill an adult if used intravenously.

Growing Nicotine

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Forms of Nicotine

United Nations

USA

Column 1
Nicotine (gum) 1996
Nicotine (nasal spray) Rx
Nicotine (oral inhaler) Rx
Nicotine (patch) 1996
Nicotine (sublingual) 2002
Nicotine-containing products are regulated in the United States but unscheduled.[4][5]

Nicotine is available over-the-counter in many forms and from many types of stores. Pure nicotine-containing products such as gums and patches are regulated very differently than tobacco-containing products such as cigarettes and chewing tobacco [see Tobacco Law]. Possession of nicotine is legal, although sales of most non-tobacco nicotine-containing products are regulated by the FDA as drugs. In most states is it illegal to sell or distribute nicotine-containing products to individuals under a certain age.[/QUOTE]

EU

Legal Staus of nicotine-containing products in 15 member states of the EU:[6]

Column 1
Ingredient Austria Belgium Denmark Finland France Germany Greece Ireland Italy Netherl. Portugal Spain Sweden UK
Nicotine (gum) OTC OTC 1989 1988 1997 1994 OTC OTC OTC 1992 1995 1995 1990 1991
Nicotine (nasal spray) 2005 Rx 1999 Rx N.R. Rx Rx Rx N.R. 2000 Rx Rx Rx 2000
Nicotine (oral inhaler) OTC OTC 1996 1998 1999 2002 Rx OTC OTC 1999 Rx N.R. 1996 OTC
Nicotine (patch) OTC OTC 1993 1993 1999 1994 OTC 1996 1993 1995 Rx 1996 1993 OTC
Nicotine (sublingual) OTC OTC OTC N.R. 1999 2000 N.R. OTC 2000 Rx 2002 OTC 2001
Legal Status of Nicotine-containing products in the newer member states of the EU and some none-EU European countries:[7]

Column 1
Ingredient Bulgaria Croatia Czech Republic Hungary Lithuania Norway Poland Slovak Republic Slovenia Switzerland
Nicotine (gum) OTC OTC OTC OTC OTC OTC OTC OTC OTC
Nicotine (nasal spray) N.R. N.R. N.R. N.R. Rx OTC N.R. N.R. Rx
Nicotine (oral inhaler) N.R. OTC N.R. N.R. OTC OTC N.R. N.R. Rx
Nicotine (patch) OTC OTC OTC OTC OTC OTC OTC OTC 2000
Nicotine (sublingual) N.R. N.R. N.R. N.R. N.R. OTC Rx N.R. OTC

Other Countries

Column 1
Ingredient Argentina Australia Canada Chile China Japan Korea Mexico New Zealand Philippines Singapore
Nicotine (gum) OTC 1988 1992 Rx 2008 2001 OTC OTC OTC N.R. 2002
Nicotine (nasal spray) N.R. OTC 2003 N.R. N.R. N.R. N.R. N.R. OTC N.R. N.R.
Nicotine (oral inhaler) N.R. OTC 2003 N.R. N.R. N.R. N.R. 2002 OTC N.R. 2002
Nicotine (patch) OTC 1997 1998 Rx 2008 2008 OTC 1998 OTC N.R. 1999
Nicotine (sublingual) N.R. OTC 2006 N.R. Rx N.R. N.R. N.R. OTC Rx 2002
Code for the above tables:
Column 1
OTC = Non-prescription status
Year = Year in which the change to non-prescription status took place
Rx = Prescription only status
N.R. = Not registered or not marketed

History of Nicotine

Nicotine, via tobacco, was first introduced to the Western World in the 16th Century, but had been used for centuries prior by the Native Americans for recreational and spiritual purposes.

Miscellaneous Information on Nicotine:

The half-life of nicotine is 2 hours.
Nicotine is metabolised in the body by the liver.

Nicotine Addiction(smoking cessation aids)

There are many smoking cessation aids on the market: nicotine lozenges, which are dissolved in the mouth (preferably the cheek where nicotine is absorbed quicker) and microtabs, which are dissolved under the tongue:
Nicotine patches, which are transdermal (absorbed through the skin) and are adhesive-backed. These are usually applied to the arm once daily, although can also be used on the legs or torso. Patches come in a variety of strengths and can be coloured flesh-tone or clear. Some are 24-hour, some are 16-hour.
There are also "e-cigarettes", used to inhale nicotine from a cartridge.
There is also nicotine chewing-gum which again comes in a range of strengths and flavours, and a nicotine nasal spray.

Also available, on prescription in many countries, are tablets used as smoking cessation aids. These are Varenicline (Chantix),[8] a smoking cessation medication given for 12 or 24 weeks, and Bupropion (Zyban)[8], an antidepressant of the NDRI class that can reduce cravings.

These medications should be researched thoroughly before being considered a personal choice, as they can have their own side effects.

It is important to remember that these smoking-cessation aids still carry a risk of nicotine overdose if abused and should only be used either as quitting smoking aids or in places where smoking would be inappropriate and/or illegal.
Smoking is not advisable whilst using smoking cessation products, particularly transdermal patches, and certainly people using smoking cessation productsshould not smoke as if not on NRT (Nicotine Replacement Therapy) as this too carries some risk of nicotine overdose, and also increases nicotine levels in the blood, making it in turn more difficult to quit nicotine addiction.
Also wearing a nicotine patch while sleeping can result in disturbed sleep and/or lucid dreaming.

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References

  1. ^Symptons of nicotine overdose: medlineplus
  2. ^LD50s of nicotine: Inchem study on nicotine: http://www.drugs-forum.com/forum/loc...tid=98&id=8888
  3. ^Nicotiana Tabacum image: http://www.tuninst.net/MyanMedPlants...acum-parts.jpg
  4. ^Quote on USA regulation of nicotines products: erowid
  5. ^Legal status of nicotine-containing products in the USA:http://www.drugs-forum.com/forum/loc...tid=15&id=8839
  6. ^Legality of nicotine-containing products in the EU: http://www.drugs-forum.com/forum/loc...tid=15&id=8744
  7. ^Legality of nicotine-containing products in newer EU and none-EU European countries:http://www.drugs-forum.com/forum/loc...15&linkid=8828
  8. ^ a bDrugs.com

[1]Merck Index, fifteenth edition (2013)
[2]Calculated from Atomic Weights of the Elements, 2007

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