
Dihydrocodeine
Dihydrocodeine | |||||||||||||||||||||||||
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Chemical Nomenclature | |||||||||||||||||||||||||
Common names | Dihydrocodeine | ||||||||||||||||||||||||
Systematic name | 4,5-alpha-epoxy-3-methoxy-17-methylmorphinan-6-ol | ||||||||||||||||||||||||
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Psychoactive class | Opioid | ||||||||||||||||||||||||
Chemical class | Morphinan | ||||||||||||||||||||||||
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Template:Proofread Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain, severe shortness of breath, or as an antitussive (either alone or compounded with paracetamol or aspirin). It was developed in Germany in 1908 and first marketed in 1911.[1]
Dihydrocodeine is also known as Drocode, Paracodeine and Parzone. Its many brand names include Synalgos DC, Panlor DC, Panlor SS, Contugesic, New Bron Solution-ACE, Huscode, Drocode, Paracodin, Codidol, Dehace, Didor Continus, Dicogesic, Codhydrine, Dekacodin, DH-Codeine, Didrate, Dihydrin, Hydrocodin, Nadeine, Novicodin, Rapacodin, Fortuss, Paramol, Remedeine, Dico and DF-118.
Dihydrocodeine is available as tablets, solutions, elixirs, and other oral forms. In some countries, the drug is available as an injectable solution for deep subcutaneous and intra-muscular administration. As with codeine, intravenous administration should be avoided as it could result in anaphylaxis and dangerous pulmonary edema. Dihydrocodeine is available in suppository form on prescription.
Dihydrocodeine is used as an alternative or adjunct to codeine and is similar in chemical structure. Depending on individual metabolism, dihydrocodeine is 100 to 150 percent as strong as codeine. Although dihydrocodeine does have extremely active metabolites in the form of dihydromorphine and dihydromorphine-6-glucuronide (one hundred times more potent), these metabolites are produced in such a small amount that they do not have clinically important effects.[2]
Dihydrocodeine is also the original member and chemical base of a number of similar semi-synthetic opiates such as acetyldihydrocodeine, dihydrocodeine enol acetate, dihydroisocodeine, nicocodeine, and nicodicodeine.
Chemistry
Dihydrocodeine shares similar chemical structure to codeine, but lacks the double bond. This results in a much more stable chemical structure and also affects its metabolism. Dihydrocodeine can be synthesised from morphine by reduction of the 7,8-double bond. It readily converts to dihydromorphine with high yields (>95%).
Pharmacology
Dihydrocodeine produces effects that are typical of μ-opioid agonists which suggests that it is pharmacologically similar to more traditional opioids such as codiene and morphine. These all appear to mimic endogenous endorphins. Endorphins are responsible for analgesia (reducing pain), causing sleepiness, and feelings of pleasure. They can be released in response to pain, strenuous exercise, orgasm, or excitement. This mimicking of natural endorphins results in the drug's euphoric, analgesic (pain relief), and anxiolytic (anti-anxiety) effects. Dihydrocodeine is metabolized via CYP2D6 to the active metabolite dihydromorphine, which has a potency similar to morphine. Other weakly active metabolites include nordihydrocodeine (which is formed via CYP3A4) and dihydrocodeine-6-glucuronide. [3]
Subjective effects
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely if ever occur all at once but heavier dosages will increase the chances and are more likely to induce a full range of effects.
Physical effects
- Pain relief - This component is subjectively different from other anaesthetics as it does not necessarily remove the pain entirely whilst still remaining equal in terms of its effectiveness. Instead of directly suppressing pain, these substances simply dull the perceived sensation and cover it up with feelings of physical and emotional pleasure.
- Euphoria - This particular substance can be considered as less intense in its physical euphoria when compared with that of morphine or diacetylmorphine (heroin) due to the upper limit of how much can be converted into its active form through metabolism. In comparison to codiene the euphoria can be described as less physically warm.
- Itchiness - It presents lower amounts of itchiness due to lower amounts of histamine release and is considerably less sedating than that of oxycodone and hydrocodone.
- Respiratory depression - At low to moderate doses, this effect results in the sensation that the breath is slowed down mildly to moderately, but does not cause noticeable impairment. At high doses and overdoses, opioid-induced respiratory depression can result in a shortness of breath, abnormal breathing patterns, semi-consciousness, or unconsciousness. Severe overdoses can result in a coma or death without immediate medical attention.
- Constipation
- Cough suppression
- Difficulty urinating
- Nausea
- Stomach cramps
- Sedation
- Pupil constriction
Cognitive effects
- Euphoria - This particular substance can be considered as less intense in its cognitive euphoria when compared with that of morphine or diacetylmorphine (heroin) due to the upper limit of how much can be converted into its active form through metabolism. It is still however capable of extreme intensity and overwhelming bliss at heavier dosages with a low tolerance.
- Anxiety suppression
- Compulsive redosing
Toxicity and harm potential
Codeine has not been shown to be toxic and is physically benign at reasonable dosages. As with all opiates, longer-term effects can vary but can include diminished libido, apathy and memory loss. Some people may also have an allergic reaction to codeine, such as the swelling of skin and rashes.[4]
Tolerance and addiction potential
Tolerance to many of the effects of codeine develops with prolonged use, including therapeutic effects. The rate at which this occurs develops at different rates for different effects, with tolerance to the constipation-inducing effects developing particularly slowly for instance.
As with other opiate-based pain killers, chronic use of codeine can be considered as highly addictive and is capable of causing both physical and psychological dependence. When physical dependence has developed, withdrawal symptoms may occur if a person suddenly stops their usage.
Legal issues
Hong Kong
In Hong Kong, dihydrocodeine is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. It can only be used legally by health professionals and for university research purposes. A pharmacist can dispense Dihydrocodeine when furnished with a doctors prescription. Anyone who supplies the substance without a prescription can be fined $10000 (HKD). The penalty for trafficking or manufacturing the substance is a $5,000,000 (HKD) fine and life imprisonment. Possession of the substance for consumption, without a licence from the Department of Health, is illegal and carries a $1,000,000 (HKD) fine and/or 7 years imprisonment.
Japan
In Japan, dihydrocodeine is available without a prescription; used in cough medicines such as New Bron Solution-ACE. Dihydrocodeine is used as an antitussive in many products as a Dextromethorphan alternative. Medicines in Japan which contain dihydrocodeine are coupled with caffeine to offset the sedative effects and discourage recreational use. Cough medicines containing dihydrocodeine are controlled similarly to dextromethrophan in the United States, in that its sale is strictly limited by purchase quantity and is restricted to persons 20 and older for purchase.
United Kingdom
In the United Kingdom, dihydrocodeine is a Class B drug; but, it is available over-the-counter in small amounts (less than 8 mg), when combined with paracetamol (see co-dydramol). Dihydrocodeine is listed in Schedule 5 of the Misuse of Drugs Regulations 2001 whereby it is exempt from prohibition on possession provided that it is in the form of a single preparation not being designed for injection and less than 100 mg (calculated as free base) or with a total concentration less than 2.5% (calculated as free base). Illegal possession of dihydrocodeine can result in up to 5 years in prison and/or an unlimited fine.
United States
In the USA, dihydrocodeine is a DEA Schedule II substance, although preparations containing small amounts of dihydrocodeine are classified as Schedule III or Schedule V, depending on the concentration of dihydrocodeine relative to other active constituents, such as paracetamol (acetaminophen). This scheduling is similar to the UK's. The DEA's ACSCN for dihydrocodeine free base and all salts is 9120. The 2013 annual aggregate manufacturing quota is 250 kilos.
See also
References
- ↑ http://books.google.co.uk/books?id=qoyYobgX0uwC&pg=PA404&lpg=PA404&dq=dihydrocodeine+1908+1911&source=bl&ots=Y7ALb1Yqjo&sig=FIkb3K4UwiXhn8LeO2EzXgxOGQk&hl=en&sa=X&ei=-mq9UsT5J4a10QXT0ID4CQ&ved=0CEQQ6AEwAzgK#v=onepage&q=dihydrocodeine%201908%201911&f=false
- ↑ The role of active metabolites in dihydrocodeine effects | http://www.ncbi.nlm.nih.gov/pubmed/12665158
- ↑ Kirkwood LC, Nation RL, Somogyi AA. Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997;44:549-55.
- ↑ http://www.drugs.com/codeine.html