Propylhexedrine
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Propylhexedrine
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| Systematic (IUPAC) name | |
| N,α-dimethyl-cyclohexylethylamine | |
| Identifiers | |
| CAS number | |
| ATC code | ? ? |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C10H21N |
| Mol. mass | 155.29 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C |
| Legal status |
Unscheduled (US Federal) |
| Routes | Nasal inhaler |
Propylhexedrine, also known as hexahydro-desoxyephedrine, hexahydro-methamphetamine, or dimethyl-cyclohexane-ethanamine, is a sympathomimetic with varied medicinal uses, is an adrenergic compound used mainly to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis. Being a vasoconstrictor used to decongest nasal mucosa, it is administered by inhalation. Propylhexedrine is most commonly found in over the counter Benzedrex inhalers and is similar to norepinephrine and epinephrine [1]. Benzedrex was first manufactured by Smith, Kline and French after the Benzedrine inhaler which contained amphetamine, became unavailable after the placement of amphetamines on Schedule II status (highest abuse potential of all legal drugs).
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[edit] Recreational use
Benzedrex inhalers are sometimes used to obtain the propylhexedrine freebase in the cotton rods they contain, as the propylhexedrine is sometimes used as a recreational drug. The effects of recreational usage are likened by some users to methamphetamine and other stimulant drugs. Among users, propylhexedrine bearing inhaler cottons, preparations or extracts are known colloquially as "Glow".
[edit] Effects
The effects of propylhexedrine are similar to ephedrine or weak methamphetamine and the effects usually vary from person to person. Propylhexedrine has been prescribed orally as an anorectic in Europe as Eventin.[citation needed] Effects include increased sweating, talkativeness, euphoria, pupil dilation, emotional lability, anorexia, tachycardia, palpitations, dry mouth, teeth grinding, anxiety, dysphoria, increased aggressiveness, paranoia, headache, dizziness, slurred or impaired speech, and rarely convulsions, serious heart problems, and psychosis can occur. Withdrawal effects can occur and can include fatigue, depression, suicidal tendencies, extreme desire for sleep, and hunger.
[edit] Injection risks
While propylhexedrine is limited in number of administration routes, attempts to extract the drug from the nasal inhaler and then inject it have been reported. Recreational use by injection is dangerous and could result in serious bodily harm or death. IV use of propylhexedrine is known to cause transient diplopia and brainstem dysfunction, and deaths have been recorded in the medical literature. Typically, recorded cases of IV propylhexedrine use were prepared by forming propylhexedrine HCl in a solution with hydrochloric acid and then the solution is heated to evaporate and the resulting crystals are dissolved in water and the resulting water injected.[2][3][4]
[edit] Recreational use potential
Propylhexedrine has a lower potential of abuse than amphetamines. This is due partially to the fact that propylhexedrine has limited methods of use, unlike more commonly abused stimulants such as amphetamine, methamphetamine, and methylphenidate. Also the fact that the only practical method of ingestion is orally means the inactive ingredients in a Benzedrex inhaler, menthol and lavender oil are also ingested which for most users is reported to be very unpleasant in taste and in smell and once consumed users report "menthol burps", frequent belching releasing the smell of the two and often causing the user discomfort and sometimes nausea. The abuse potential is low enough that neither the DEA nor the WHO consider it a drug of concern at the present, unlike ephedrine or its salts which are of concerns as precursor chemical to manufacture of primarily methamphetamine or occasionally amphetamine.
[edit] Drug risks
As with similar drugs, using propylhexedrine to keep oneself awake for extended amounts of time can lead to a temporary state of sleep deprivation possibly similar to an amphetamine psychosis during which an individual may experience hallucinations including auditory, visual, and tactile (e.g. bugs crawling on or under the skin), paranoia, irritability, and impaired memory.
Propyhexedrine being a vasocontrictor and being a stimulant causes further risk as blood pressure and heart rate are raised, sometimes severely. Hypertension experienced by users of propylhexedrine can be dangerous, especially in those who have pre-existing blood pressure problems. Also, the increase in heart rate can lead to lower levels of oxygen, discomfort, panic and in severe cases heart attack or serious arrhythmias. Again this risk is higher if the user has existing heart problems. Taking propylhexedrine and MAOIs together can lead to a fatal hypertensive crisis. Also, propylhexedrine ingested along with other stimulants like amphetamines, caffeine, and cocaine can lead to adverse effects, such as serious hypertension and a significant increase in heart rate. It would be wise to avoid ingesting any substance along with propylhexedrine, including all recreational drugs, OTC drugs, prescription drugs, and herbal products, as interactions with proyplhexedrine are largely unknown.
Eating the cotton also has its own risks, and while ingesting cotton is not necessarily fatal, it can still lead to severe gastrointestinal problems, which may require medical attention. Potential problems include cramps, gas, and temporary constipation. More serious problems can include gastric blockages and internal infection. Some users try and reduce this risk by shredding the cotton into multiple pieces and swallowing at intervals. Whether or not this reduces the risk is unknown. One way to avoid bowel blockages is to form an active salt of propylhexedrine and discarding the cotton. Another common, and easy, method of propylhexedrine extraction is soaking the cotton rod in lemon juice, shaking the concoction for a few minutes, then straining the mixture into a glass containing some sort of neutral carbonated beverage, then drinking the liquid solution. This method is very favorable over ingesting the pure cotton.
[edit] Chemistry
Propylhexedrine is structurally similar to methamphetamine. The only difference is that the phenyl group of the methamphetamine molecule is swapped with a cyclohexyl group. It is because of this that propylhexedrine is not an amphetamine, nor even a phenethylamine. It is most like methamphetamine in terms that it contains a methyl (CH3) group in positions Rα and RN.
Propylhexedrine, like amphetamine and methamphetamine, is a chiral compound (the α-carbon is chrial, like in its amphetamine cousins). Like other monoamine releasing stimulants with the amphetamine type backbone, the dextrorotatory isomer of propylhexedrine is much more active as a norepinephrine and dopamine releaser in the central nervous system than the levorotatory isomer is. The propylhexedrine contained in Benzedrex inhalers is racemic d,l-propylhexedrine as the freebase. It is likely that pure d-propylhexedrine would have a higher abuse potential and less undesirable side effects than the racemic compound.
Freebase d,l-propylhexedrine is a volatile, oily liquid at room temperature. This is the form present in Benzedrex nasal inhalers; the volatility of the freebase form insures that some propylhexedrine will be inhaled from the device when used as indicated on the label. D,l-propylhexedrine hydrochloride is a white powder if finely ground, or a clear crystalline substance if the crystals grown are larger. The hydrochloride salt can be vaporized much like the hydrochloride salt of methamphetamine can be.
Propylhexedrine is an amine, and is thus an organic base. Amines are essentially ammonia with one of the hydrogens substituted with an organic moiety; from a different perspective, they're organic compounds with ammonia bound to them by switching out one of the hydrogens on ammonia and one on a carbon to form a carbon to nitrogen bond. Amines thus behave like ammonia does as a base, with some exceptions (one is the case where the free electron pair on the nitrogen atom is close to or part of an aromatic ring; the free electron pair can become delocalized into the aromatic pi bonding system of the ring which reduces potency as a base of the amine). The free electron pair on the nitrogen atom can form a coordinate covalent bond with H+ ions (protons), and protons are one of the ions released into solution when an acid is dissociated in water (the other is the counterion of the acid which carries a negative charge). Thus, ammonia and amines are bases according to the Lewis theory of acids and bases, meaning that they're compounds which can accept a proton (in this case by forming a coordinate covalent bond with it). The result with ammonia is the ammonium cation NH4+ (the anion remains unchanged). So for hydrochloric acid, the reaction with ammonia would look like this:
NH3(aq) + HCl(aq) --> NH4Cl(aq)
If the water is evaporated the solid salt ammonium chloride would result.
With amines a reaction analogous to the one with ammonia occurs, with the difference being that one of the ammonia's hydrogen atoms is replaced with an organic moiety:
Propylhexedrine + HCl(aq) --> Propylhexedrine HCl (aq)
or to more clearly convey what occurs, using the IUPAC name N,α-dimethyl-cyclohexylethylamine for propylhexedrine --
N,α-dimethyl-cyclohexylethyl-NH2 + HCl(aq) --> N,α-dimethyl-cyclohexylethyl-NH3+ *Cl- (aq)
The asterisk (*) indicates an ionic bond which will form upon evaporation of the water.
Although propylhexedrine as the freebase is insoluble in water, an acid solution in water like hydrochloric acid will react with the propylhexedrine layer and pull it into the aqueous phase once it is protonated.
Upon evaporation of a solution of propylhexedrine hydrochloride, the solid, white / clear, crystalline hydrochloride salt of propylhexedrine will result.
[edit] See also
[edit] References
- ^ http://www.medications.com/drugs/benzedrex
- ^ "Proposed Rules". Federal Register 50 (10): 2226 – 2227.
- ^ Prince v. Ascher, 90 P.3d 1020 (2004).
- ^ Fornazzari L, Carlen PL, Kapur BM. "Intravenous abuse of propylhexedrine (Benzedrex) and the risk of brainstem dysfunction in young adults." Canadian Journal of Neurological Science. 1986 Nov;13(4):337-9. PMID 2877725
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