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Dimethocaine - the "larrikin" relative of cocaine

phase_dancer

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From user reports, Dimethocaine HCl appears to be available in Australia. It could be used to cut cocaine, or mixed with other drugs/cuts etc , or sold straight. It has been referred to as 'legal cocaine' and seems to have acquired the street name larrikin (no doubt after the name generic name larocaine).


Background


As the unwanted side effects of cocaine were apparent early on, synthetic anaesthetics were developed shortly after its structure had been determined. Eucaine was first synthesised in 1859, but proved too toxic. Elucidation of the essential part of the cocaine molecule led to piperocaine, which was non-habit forming and less toxic than cocaine. Procaine was eventually developed and used for many years, again because of its non-habit forming properties and low toxicity (~1/4 that of cocaine). Like several of the synthetic anaesthetic esters, Procaine contains an para-amino substituted aromatic ring. Other para amino esters include Benzocaine with a 2 carbon tail, and tetracaine with an n-butyl group.

220px-Procaine_Structural_Formulae.png
Procaine

220px-Benzocaine.svg.png
Benzocaine

220px-Tetracaine.svg.png
Tetracaine


Dimethocaine was developed as a anaesthetic, although it's not commonly used for this purpose, if at all. It wouldn't have been a popular candidate for anaesthesia as it pales next to some other esters and has relatively high CNS activity.


Pharmacology


At first glance it might appear dimethocaine has little in common with cocaine apart from the benzoate group i.e. the carbonyl group attached to the aromatic ring.

220px-Dimethocaine.png
Dimethocaine

cocaine_2d.gif
Cocaine


As said, the benzoate ester is a common feature of many of the synthetic anaesthetics. The side chain of the ester could be a simple carbon chain as in benzocaine, a linear chain tertiary amine as with procaine, or a branched chain as with dimethocaine. If a tertiary amine is present, one of the condition necessary for CNS activity is the correct proximity of the amine to the carbonyl oxygen and the carboxyl oxygen. The branched chain of dimethocaine threfore places the amine in a spatially similar position to the azabicyclo nitrogen of cocaine.

dimethocaineoncocaineqs0.jpg


As can be seen, the 3D or spatial model of cocaine superimposes quite well over that of dimethocaine (
14.gif
for the image Hammilton) indicating it could act like cocaine in terms of its CNS activity; binding to DAT and preventing DA uptake.

Dimethocaine is reportedly ~ 1/3 to 1/2 the potency of cocaine, and produces a similar euphoria, although some people claim a noticeable difference. From the user reports on BL, most people agree the effects last 1- 1/2 hours, then abruptly cease.

http://www.bluelight.ru/vb/search.php?searchid=4086599

Metabolism

Cocaine and the synthetic ester ‘caines’ are chiefly metabolised via hydrolysis, and dimethocaine is expected to be handled in a similar manner, producing 4-amino benzoic acid (aka para-aminobenzoic acid or PABA) and 3-(diethylamino)-2,2-dimethylpropanol.

PABA is produced in humans from bacteria in the bowel. It was also once used extensively as a UV filter in sunscreen, however, it was found that PABA increases the formation of a DNA defect and increases the risk of skin cancer. In some animals (not humans) it is a biological precursor for folate. PABA toxicity (in-vivo uses) has been noted in humans but most cases resulted from consuming large amounts (>10g/day) as a supplement. Some health companies state PABA stimulates healthy bowel flora when taken orally but there’s little evidence to back this up. Anyway, for most people this metabolite shouldn’t prove too troublesome with reasonable use patterns.

There is little available on the actions and toxicity of the second primary metabolite -- 3-(diethylamino)-2,2-dimethylpropanol. It was researched as a possible anti-tumour agent, but was found to be ineffective (check pub-med for review summary). With what’s available on this compound it’s impossible to fully deduce what possible problems it could cause. It’s expected 3-(diethylamino)-2,2-dimethylpropanol will be oxidised to the carboxylic acid and readily excreted (Note; comments welcome here)

Genetic Predisposition

A particular health concern needs to be mentioned first, although is not likely to affect many users. Those suffering from a condition known as Pseudocholinesterase Deficiency must avoid the use of many drugs, particularly esters that are metabolised by this enzyme. For PD sufferers, taking such drugs can result in severe, life threatening situations (see wiki entry for Pseudocholinesterase deficiency). While the disease is generally rare, above normal prevalence among some ethnic groups has been noted.

Toxicity

The other, perhaps more relevant health concern involves the basic actions of the drug - the anaesthetic and CNS effects. Coke causes many problems in this regard, with hospital admissions due to heart related problems common with long term/ heavy use. Those with underlying heart conditions are particularly at risk, possibly even from relatively low and infrequent dosages. From first appearances it was thought dimethocaine could have anaesthetic actions equal or greater than an equivalent dose of cocaine. Thankfully, it would appear it only has around half the anaesthetic potency of cocaine, but that doesn't mean it's safe. While internet prices for dimethocaine HCl vary greatly, it can currently be sourced from some chem suppliers at a fraction of the price of cocaine, which could well mean larger dosages are consumed (remember you need around twice that of cocaine for a similar effect). So, the warnings in relation to the dangers of cocaine also apply here. It may even turn out that dimethocaine is far more toxic to the heart, but there seems to have been little research done in this area so no-one really knows.

Cocaine is also known to cause many health problems, particularly with heavy use. It can be reasonably expected that many of these could also apply to dimethocaine use, perhaps even at lower dosages.

Identification

Cocaine can be subjected to various tests to evaluate it's purity. Scott's test (cobalt thiocyanate) can test for the presence of coke but it also reacts with some other compounds, and potassium thiocyanate is said to be able to evaluate the purity of cocaine. But by far the most common tests done are melting point and the Chlorox or bleach tests. In the past these have been considered a fairly reliable means of establishing purity, particularly when both tests are performed. However, dimethocaine has a melting point very close to that of cocaine (196-197°C and 195°C respectively). Reports indicate dimethocaine may also fool the bleach test.

In looking for a suitable reagent test for dimethocaine, the para-amino group is a good target, but unfortunately most tests involve the use of toxic or difficult to handle chemicals. One of the least dangerous of the reagent tests involves the use of Coniferyl alcohol. 0.3 g is heated until it melts, then dissolved in a few mls of ethanol, and diluted to 10ml. A drop of a solution of the sample is placed on filter paper, the coniferyl alcohol soln added, and the paper exposed to HCl vapours.

Legality

As mentioned, in terms of spatial orientation, dimethocaine is certainly a structural analogue of cocaine. However, in terms of the respective functional groups there is quite a difference. Cocaine is a di-ester, dimethocaine isn't. Cocaine has a tropane ring, whereas dimethocaine has a branched, alkylamine, and dimethocaine has an aromatic amine, where coke doesn't.

To my limited understanding of legal things, I would imagine this could prove to be a technical hurdle for prosecutors, and may require testament on the pharmacological similarities in order to convict. Has a precedent ever occurred in Australia where substantially similar pharmacological actions have been successfully used? If not, it may well have to be if prosecutions result from dimethocaine use. And this stuff is undoubtedly only the beginning. There are countless possibilities here, some of which will again be considerably different in terms of the functional group/placement and structure.


It would be good to hear the thoughts of some of our BLers more familiar with analogue legislation; fortehlulz, Tabaluga, Biscuit.... and from anyone with reports of dimethocaine use, particularly in regards to any observed side effects, interactions with other drugs etc.
 
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nabollocks

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PD, there has been some talk of this substance over in ADD.

Approx 0.25-0.5x cocaine.

I sort of wish it had not have been brought up here in AusDD, but I guess it is for the best. (In terms of HR)
 

Crankinit

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Very informative thread.

I'm interested though, when people say 50% the potency of cocaine, does that just mean that you need double the doseage to get the same subjective high, or that even at the 'standard recreational dose' you'll still only be half as high as you would on coke? I suspect the former, but this has piqued my curiosity.
 

nabollocks

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Something tells me that PD was a bit of a larrikin back in the day...;)
 

static_mind

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Iv heard and known of users who have had "synthetic coke". They said it felt simmiler but different to coke.

Who knows, could be it.
 

nabollocks

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Iv heard and known of users who have had "synthetic coke". They said it felt simmiler but different to coke.

Who knows, could be it.

Generally Mephedrone is called "synthetic coke" in the media.

The chemical PD is referring to is something quite different. It is sold in many head shops in Europe as a legal high.
 

Crankinit

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The consensus seems to be around 100mg is required for a noticeable, cocaine like effect.

Yes but with the way Aussie street coke is these days, you need 200mg to get a noticeable, cocaine like effect from actual cocaine :p

The 60 - 90 minute duration is a huge plus as well, one of the downsides of coke is having to redose every 20 minutes.

Not liking the look of that cardiotoxicity though. Why can't someone find a cocaine analogue that has the same psychoactive effect but isn't so hard on the heart?

Actually that makes me curious, is cardiotoxicity intrinsinc to any chemical that is both a CNS stimulant and an anaesthetic, or is there something specific about the -caine drugs that cause that effect?

Also, does dimethocaine metabolize into another chemical when consumed with alcohol ala. cocaine/cocaethelyne?
 

phase_dancer

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Not liking the look of that cardiotoxicity though. Why can't someone find a cocaine analogue that has the same psychoactive effect but isn't so hard on the heart?

Actually that makes me curious, is cardiotoxicity intrinsinc to any chemical that is both a CNS stimulant and an anaesthetic, or is there something specific about the -caine drugs that cause that effect?

Unfortunately the anaesthetic esters are all likely to present some cardiotoxicity. CNS active amides may be better in this regard, but many could also be hepatotoxic (toxic to the liver).

Also, does dimethocaine metabolize into another chemical when consumed with alcohol ala. cocaine/cocaethelyne?

It wouldn't form a compound analogous to ethyl cocaine. If you look at the cocaine molecule you'll see it's a di-ester, containing the benzoate ester and the ecgonine methyl ester. Carboxylesterases cause the ecgonine ester to undergoe transesterfication when both ethanol and cocaine are present in the liver. This enzyme also plays some role in procaine (and probably cocaine and dimethocaine) metabolism, hydrolysing the benzoate ester. It's possible that if ethanol and dimethocaine are taken together that some may result in transesterfication, which would produce benzocaine, but I'm not sure this would happen in significant amounts. If it did, I would suspect there'd be little interest in dimethocaine from the drinking side of cocaine users.

Another interesting ester is produced with cocaine if methanol is used in certain stages of cocaine production or when cocaine HCl absorbs moisture. The acid catalysed hydrolysis sees some of the cocaine destroyed as both ester linkages are cleaved. One of the products is methyl benzoate (oil of Niobe) which gives cocaine it's characteristic odour (similar to feijoas). Methyl benzoate is highly detectable to both humans and dogs. I remember reading an article some years back claiming humans had close to the same olfactory sensitivity for the compound.

It would be relatively easy to mix dimethocaine with methyl benzoate and sell it as real cocaine, so, if the drug does take off, a good detection method might be invaluable for those who only want the real thing.
 

marklar_the_23rd

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i must be one of those "hard heads" shulgin talks about but i found it only got fun when i'd had about 200 - 300 mgs.

it acts like coke too - needs a warm plate - but it has a smell "like a wet vagina" according to one of my friends who takes coke. but the effect, to him, wasn't as good, but similar.
 

bit_pattern

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Identification

Cocaine can be subjected to various tests to evaluate it's purity. Scott's test (cobalt thiocyanate) can test for the presence of coke but it also reacts with some other compounds, and potassium thiocyanate is said to be able to evaluate the purity of cocaine. But by far the most common tests done are melting point and the Chlorox or bleach tests. In the past these have been considered a fairly reliable means of establishing purity, particularly when both tests are performed. However, dimethocaine has a melting point very close to that of cocaine (196-197°C and 195°C respectively). Reports indicate dimethocaine may also fool the bleach test.

In looking for a suitable reagent test for dimethocaine, the para-amino group is a good target, but unfortunately most tests involve the use of toxic or difficult to handle chemicals. One of the least dangerous of the reagent tests involves the use of Coniferyl alcohol. 0.3 g is heated until it melts, then dissolved in a few mls of ethanol, and diluted to 10ml. A drop of a solution of the sample is placed on filter paper, the coniferyl alcohol soln added, and the paper exposed to HCl vapours.

Sorry don't know much about reagents but are any of these the new EZ White testers?
 

lewk

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I have noticed that Dimethocaine has become scarcely available in Australia but available none-the-less.. i was hoping someone would be able to clear this up..

The import prohibition for Cocaine in Australia covers:

including the leaf of any plant of any species of the genuserythroxylon from which cocaine can be extracted, either directly or by chemical transformation

Would that mean it includes Dimethocaine? Is it achieved by chemical transformation?

Found an extract from the Drug Misuse and Trafficking Act 1985 that someone had already talked about in regards to a different chemical..

Prohibited plant or prohibited drug

Any substance that is an analogue of a drug prescribed in this Schedule, being a substance that has psychotropic properties, is not separately specified in this Schedule and is, in relation to the drug, any of the following:

(a) a structural isomer having the same constituent groups as the drug,

(b) a structural modification obtained in one or more of the following ways:

(i) the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures,

(ii) the addition of hydrogen atoms to 1 or more unsaturated bonds,

(iii) the addition of 1 or more of the following groups having up to 6 carbon atoms in any alkyl residue, namely, alkoxy, cyclic diether, acyl, acyloxy, monoalkylamino and dialkylamino groups,

(iv) the addition of 1 or more of the following groups having up to 6 carbon atoms in the group and being attached to oxygen, namely, alkyl, alkenyl and alkynyl groups (for example, ester groups and ether groups),

(v) the addition of 1 or more of the following groups having up to 6 carbon atoms in the group and being attached to nitrogen, sulphur or carbon, namely, alkyl, alkenyl and alkynyl groups,

(vi) the addition of 1 or more of the following groups, namely, halogen, hydroxy, nitro and amino groups,

(vii) the replacement of 1 or more of the groups specified in subparagraphs (iii)–(vi) with 1 or more other groups so specified,

(viii) the conversion of a carboxyl or an ester group into an amide group

I can't say i'm too familiar with chemistry or related topics, but my guess is Dimethocaine would fall under one of those?
 
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phase_dancer

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Lewk said:
I have noticed that Dimethocaine has become scarcely available in Australia but available none-the-less.. i was hoping someone would be able to clear this up..

The import prohibition for Cocaine in Australia covers:

including the leaf of any plant of any species of the genuserythroxylon from which cocaine can be extracted, either directly or by chemical transformation


Would that mean it includes Dimethocaine? Is it achieved by chemical transformation?

Dimethocaine isn't chemically similar to anything produced by coca, or any chemical produced by altering or transforming anything found in a coca extract. Dimethocaine is a synthetic, and to my knowledge isn't produced in nature.



Found an extract from the Drug Misuse and Trafficking Act 1985 that someone had already talked about in regards to a different chemical..


Prohibited plant or prohibited drug

Any substance that is an analogue of a drug prescribed in this Schedule, being a substance that has psychotropic properties, is not separately specified in this Schedule and is, in relation to the drug, any of the following:

(a) a structural isomer having the same constituent groups as the drug,

(b) a structural modification obtained in one or more of the following ways:

(i) the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures,

(ii) the addition of hydrogen atoms to 1 or more unsaturated bonds,

(iii) the addition of 1 or more of the following groups having up to 6 carbon atoms in any alkyl residue, namely, alkoxy, cyclic diether, acyl, acyloxy, monoalkylamino and dialkylamino groups,

(iv) the addition of 1 or more of the following groups having up to 6 carbon atoms in the group and being attached to oxygen, namely, alkyl, alkenyl and alkynyl groups (for example, ester groups and ether groups),

(v) the addition of 1 or more of the following groups having up to 6 carbon atoms in the group and being attached to nitrogen, sulphur or carbon, namely, alkyl, alkenyl and alkynyl groups,

(vi) the addition of 1 or more of the following groups, namely, halogen, hydroxy, nitro and amino groups,

(vii) the replacement of 1 or more of the groups specified in subparagraphs (iii)–(vi) with 1 or more other groups so specified,

(viii) the conversion of a carboxyl or an ester group into an amide group


I can't say i'm too familiar with chemistry or related topics, but my guess is Dimethocaine would fall under one of those?

As Dimethocaine is not a chemical analogue of a scheduled substance, I'd doubt the above functional group changes could ever be applied. However, the above excerpt doesn't include the other subsections typical of analogue legislation in this country, one of which relates to whether a compound is substantially similar in chemical structure to a controlled drug.

As I've outlined in the opening post, it's difficult to say, because chemically (functional groups etc), they are very different beasts, but from a 3D structural perspective, they're very similar. If a court case came up where there was attempt to use this legislation, I'd imagine the prosecution would have a pharmacologist explain similarity as it relates to both the structural similarity of cocaine, and the predicted-expected CNS activity.

But until that's done and a precedent set, or the stuff is banned first, then no one can say just how legal dimethocaine is in Australia.
 

trippa

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hmmm very interesting. Thanks Phase Dancer ...
 
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Biscuit

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I only just noticed this.

I do not believe this substance could possibly be caught by the analogue laws with respect to cocaine. Whether it comes within the laws because it is similar to another substance, I don't know.

My guess is that unless someone was caught with a heap of this stuff the police and the prosecution would put it into the too hard basket and be done with it. They probably would not give it back to you but whether they would bother with such an involved, complicated and uncertain prosecution for such little reward is another matter. I strongly suspect not.
 

phase_dancer

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Sorry, I missed your question. Yes it does numb, but along with the CNS potency being lower than with coke, so are it's anesthetic actions.
 
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