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Metabolically stable analog of nicotine?

wungchow

wungchow

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I always thought it would be intriguing to create and market "long lasting cigarettes" which contain a nicotine analog that has a longer half-life, enabling one to smoke fewer cigarettes a day (since the frequency of smoking is what can make it so addictive.)

It is my understanding that the major metabolic pathway for nicotine is oxidation to cotinine:

nicotine.gif

nicotine

cotinine.GIF


Then, would swapping the oxygen in cotinine with a -CH3 (methylnicotine) effectively give us a much longer half-life?
 
well you'd be marketing a drug as you would need to get it approved via the country's drug approval system to market such

there are many analogues of nicotine in the literature, many created when tobacco is burned
 
what?? No way. Just because it shares a single feature in common with a much larger molecule in no way indicates it'll have similar activity.
 
Actually nicotine, cotinine and various other nACh agonists are nootropic, but by a quite different mechanism to the racetams (which are AMPA positive modulators most likely)
 
^ And they're great for my impending parkinson's. I knew I should have mentioned that, but after a different thread (I forget which), I knew where the connection was coming from and what was meant.

Is pyrrolidinone the new methylenedioxy? Only on the smart drug set? ;)
 
LuxEtVeritas said:
there are many analogues of nicotine in the literature, many created when tobacco is burned
Click to expand...

It would be difficult to know how much those analogues put the actual activity into smoking nicotine then, due to the pyrolysis of nicotine itself creating those chemicals.
 
It is my understanding that longer acting ACh agonists would not be pleasurable. Likely more of that shaky "I just smoked way too many cigarettes" feeling that lasts for ages. Besides we have longer acting deliver methods that are not very popular, cigars for example.
 
I think that would depend on potency and efficacy, and then how much is actually ingested. Varenicline doesn't seem to cause that (but isn't that a partial agonist?)
 
wungchow said:
I always thought it would be intriguing to create and market "long lasting cigarettes" which contain a nicotine analog that has a longer half-life, enabling one to smoke fewer cigarettes a day (since the frequency of smoking is what can make it so addictive.)
Click to expand...


No, what makes nicotine so addictive is that it's usually an inhaled (really fast come-up) reward system drug.

Addiction is mostly about the speed of the come-up. Duration is a factor, but nowhere near as large (injected heroin lasts 3 hours (never done, it but that's what i've been told) yet is still very addictive. However orally taken opiates that last 3 hours are nowhere near as addictive. The intensity of the high is also nowhere near as important as the speed of the come-up.

Nicotine gum is nowhere near as addictive as inhaled nicotine.
 
Cytisine (a natural alkaloid) and its bromination product are long-acting nicotinergics. Cytisine tabletts are sold by a Eastern European company for smoking cessation.
 
vinylmesh said:
No, what makes nicotine so addictive is that it's usually an inhaled (really fast come-up) reward system drug.

Addiction is mostly about the speed of the come-up. Duration is a factor, but nowhere near as large (injected heroin lasts 3 hours (never done, it but that's what i've been told) yet is still very addictive. However orally taken opiates that last 3 hours are nowhere near as addictive. The intensity of the high is also nowhere near as important as the speed of the come-up.

Nicotine gum is nowhere near as addictive as inhaled nicotine.
Click to expand...

Hey, thanks for the information. I've been in the process of quitting smoking for a few weeks now, been on the gum. I'm not heavily addicted at all, but I would like to avoid withdrawal however small it may be so I've been tapering with the gum, started with 4 a day, now I'm down to 1 or 2 a day, at 730pm today I'm just starting to get cravings, on to my point:

I noticed whilst quitting that if I chew only the gum for a good week or so, I'm very close to no withdrawals at all, but the few times I've 'relapsed', and had a drag off someone's smoke, I've noticed withdrawals much earlier the next day. I figured the Nicotine in the gum, and that in the cigarettes are going to keep me just as hooked, so having a drag for example, rather than a piece of gum is not a really big issue, turns out it probably is and I should stick 100% to the gum, eh?

Haha, quitting is hard...I'm not very addicted to 'cigarettes' I don't miss them at all, it's strictly Nicotine I seek, strictly to keep WDs away whilst I'm at school. What makes it hard is not really caring too much for my physical health, and this all just being about a 4 month, substance free vacation for the sake of my mental health. Nicotine, if anything, seems to help me mentally, my HPPD and anxiety gets pretty bad during withdrawals, and a ciggy always calms me, but alas, I shall prevail for 4 months, and probably become a smoker again when it is over, lol, making quitting quite tough.
 
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