"L" and "D" Nicotine

Status
Not open for further replies.

bassnut

Crumby Jokes
ECF Veteran
Apr 1, 2010
503
10,814
Los Angeles, CA
For the record:
Can somebody enlighten me in simple terms the difference between natural "L" nicotine and synthetic "D" nicotine and what it is we are consuming in E-juice?
...and while you're at it can somebody speak to the claim of one e-liquid supplier using (special process) something else altogether? What's the bottom line here?
 

bassnut

Crumby Jokes
ECF Veteran
Apr 1, 2010
503
10,814
Los Angeles, CA
Nope. Not innovapor that I was thinking of, 'twas the other one. I haven't checked innovapor yet.
Anyway, aren't their certain pharmaceutical standards?

I mean "L" is "L" and "D" is "D" and anything else gets a different documented name right? There's got to be some very rigid standards here. Hey, big Pharma and FDA aren't totally usless....are they?
 
Last edited:

CES

optimistic cynic
ECF Veteran
Verified Member
Jan 25, 2010
22,181
61,133
Birmingham, Al
Last edited:

DVap

Nicotiana Alchemia
ECF Veteran
Verified Member
Aug 26, 2009
1,548
1,586
There are two forms of nicotine, and chemists use different naming systems to indicate the same thing. These multiple naming systems have been annoying me since I took organic chemistry in college back in 1983.

L-nicotine
(-)-nicotine
(S)-nicotine

All three above are used to express the naturally occurring stereoisomer of nicotine in it's isolated form.

D-nicotine
(+)-nicotine
(R)-nicotine

All three above are used to express the non-naturally occurring (synthetic) stereoisoner of nicotine in it's isolated form.

If nicotine is made synthetically with equal amounts of each stereoisomer present, it is referred to as (DL)-nicotine, (RS)-nicotine, or (±)-nicotine.

Production-wise, the naturally occurring (L),(-),(S)-nicotine is what we get and what we use. Purification of this stereoisomer from tobacco is relatively easy and cheap.

Racemic nicotine (DL),(RS),(±)-nicotine, is available in mg quantities for a hefty price.

The purified non-natural stereoisomer (D),(+),(R)-nicotine is typically found only in research settings, and the price is out of this world.
 
  • Like
Reactions: Mr.Mann

bassnut

Crumby Jokes
ECF Veteran
Apr 1, 2010
503
10,814
Los Angeles, CA
Thank's DVap but can you translate that into Greek for me so I can understand it?

Just kidding. It was not difficult to feel your enthusiasm in your offering of this info. I'll bet it's the first time that it's been presented this way at ECF. It's not so hard to make history here. It's sort of like the Wild West....which may be a tired phrase already.

I think what I'm getting at...the question becoming more clear as I go along...is that nicotine from a controlled pharmaceutical source be it L or D, + or - or XYZ has got to be consistent. It's a controlled substance right?
If I go to source "A" and say sell me your best 98% to 99% pure nicotine and then find out that source "B" is claiming that their 98% to 99% purity nicotine is different or maybe....stronger!
Does anybody else see the disconnect here?
The FDA is looking to find precisely this kind of out-of-control scenario.
Please, somebody help me out here.
 

CES

optimistic cynic
ECF Veteran
Verified Member
Jan 25, 2010
22,181
61,133
Birmingham, Al
Thanks for the clarification/correction DVAP. I'm not a chemist, and was trying to make the connection between L and (-)-nicotine vs D and (+)-nicotine, and not doing very well at it. Didn't know where the S term fit.

Bassnut, nicotine isn't a 'controlled substance'. If you're ordering it it from a scientific supplier the form, the level of purity, and sometimes a product analysis sheet are all available. There are some differences in 'grade' even at the same % purity, that are related to how it was purified and that can be very important depending on why you need it. Also in a lab, the difference between 98.9% purity and 99.9% purity can be crucial.

It sounds like what you're asking is if two suppliers claim to have nicotine of the same purity, could claims to have a better product be based on using a different form/isomer of nicotine? I don't think so. If it was based on D vs L nicotine, using the D nicotine would be more expensive and be less effective. IMO The claims could be based on using molecular biology grade vs pharmacology grade, or completely different extraction methods, but it doesn't have to do with the strength of the nicotine itself.
 

bassnut

Crumby Jokes
ECF Veteran
Apr 1, 2010
503
10,814
Los Angeles, CA
Thanks, CES. I do believe that answers my question.

Here's another one:
Is there a test to determine the nicotine content of liquid? Is there some sort of PH test in the form of a plastic strip for dipping etc. available from a lab supplier?
I would imagine that most E-Liquid suppliers would have something like this for safety and quality control.
 

DVap

Nicotiana Alchemia
ECF Veteran
Verified Member
Aug 26, 2009
1,548
1,586
Thanks, CES. I do believe that answers my question.

Here's another one:
Is there a test to determine the nicotine content of liquid? Is there some sort of PH test in the form of a plastic strip for dipping etc. available from a lab supplier?
I would imagine that most E-Liquid suppliers would have something like this for safety and quality control.

Yep. Eliquid can be tested quite simply for nicotine, but not quite so simply as dipping a test strip.
 

Whistle_Pig

Ultra Member
ECF Veteran
Apr 11, 2010
1,147
62
Littleton, CO, U.S.
Yep. Eliquid can be tested quite simply for nicotine, but not quite so simply as dipping a test strip.

DVap's test method; and scroll down for more. It's a 75 page thread, and I haven't paged forward to see if there are yet more alternate methods.

(And not to imply that that's the only test method DVap has posted; I don't know that.)
 

Kurt

Quantum Vapyre
ECF Veteran
Sep 16, 2009
3,433
3,606
Philadelphia
To add to DVap's accurate info, nicotine is asymmetric. Like your hand. Your hand has no plane of symmetry where everything on one side of the plane is mirrored with everything on the other side. Your right hand is the mirror image of your left hand, and they cannot be perfectly superimposed one on the other, with all fingers matched and pointing in the same direction. Molecules can have the same type of asymmetry. D- and L-nicotine are the same molecule when drawn in two dimensions, but mirror images when drawn in 3-D. Chemically they are equal in most situations. But they are not equal when they are interacting with cell receptors, which are also asymmetric.

Much like if someone wants to shake hands with me with their right hand, the best shake will be me using my right hand. My left hand can be used, but it will not be the same full grip. But what is "right" and "left" at the molecular level?

If I make a solution of L-nicotine, it will rotate plane-polarized light shown on it to the left, that is, counter clockwise. We call this "levorotatory", or "L" for short. A solution of D-nicotine will rotate plane-polarized light to the right, clockwise. This is "dextrorotatory", or "D".

(+) and (-) are just another way of saying "D" or "L".

D- and L-nicotine are examples of enantiomers, or non-superimposable mirror-image stereoisomers. We say that nicotine is chiral, meaning "handed".

"S" and "R" are absolute molecular descriptions, and are based on the orientation of atomic groups around the chiral center, which is the asymmetric carbon. "R" means "right", but the R-enantiomer does not have to be the "D-" enantiomer. In other words, how a molecule rotates pp light does not necessarily dictate if it is R or S. "S" is the mirror image of the "R" enantiomer. "S" stands for "sinister", as in the left hand is, in the old way of thinking, the sinister hand.

L-nic is the enantiomer with the highest bio-activity, and its the enantiomer that tobacco makes. As DVap said, extraction is the cheapest and best way to get and purify it, as in pharma-grade. D-nic is wildly expensive and not what we would want anyway. Even a mixture of the two enantiomers can only be made synthetically and will still be far more expensive than just extracted L-nic. It's very nice that the cheapest is actually the best, in this case. Its not nice, however, when erroneous claims about these enantiomers are used to try to sell juice, and hopefully this is not occurring any more.
 

Kurt

Quantum Vapyre
ECF Veteran
Sep 16, 2009
3,433
3,606
Philadelphia
Thanks for the further information, Kurt.

Can I call 'em 'port' and 'starboard' instead of sinistra- and dextro- ?

Same concept as the artificial sweetener that's a flipped sugar molecule -- sucrose?

Yes, it is like dextrose (natural sucrose) vs levulose (mirror image). Same chemical and physical properties (mp, bp, solubility in water), but one is recognized as a viable energy source for the body, and the other is not. Thanks for reminding me of this example. I had forgotten about this.

Port and starboard is for right and left sides of one ship. This would be two ships that are identical in all respects save for the fact that they are mirror images of each other.
 
Last edited:

Old Chemist

Super Member
ECF Veteran
Dec 23, 2009
324
130
68
Poland
starychemik.wordpress.com
Yes, it is like dextrose (natural sucrose) vs levulose (mirror image). Same chemical and physical properties (mp, bp, solubility in water), but one is recognized as a viable energy source for the body, and the other is not. Thanks for reminding me of this example. I had forgotten about this.
Errr... are you sure? Dextrose is the synonym of D-glucose. The enantiomer would be L-glucose, not levulose.
Levulose is the synonym of D-fructose. It is one of the isomers of dextrose, but NOT the enantiomer.
Dextrose is an aldohexose, levulose is a ketohexose. They differ chemically much.

Anyway - it's good that we vape good old nicotine, not those bloody carbohydrates.
 

Whistle_Pig

Ultra Member
ECF Veteran
Apr 11, 2010
1,147
62
Littleton, CO, U.S.
Port and starboard is for right and left sides of one ship. This would be two ships that are identical in all respects save for the fact that they are mirror images of each other.

Yeah, I know. I just thought it'd be funny. Or we could use 'clockwise' and 'widdershins'. Both of which are easier to remember than levarotatory.
 

Kurt

Quantum Vapyre
ECF Veteran
Sep 16, 2009
3,433
3,606
Philadelphia
Errr... are you sure? Dextrose is the synonym of D-glucose. The enantiomer would be L-glucose, not levulose.
Levulose is the synonym of D-fructose. It is one of the isomers of dextrose, but NOT the enantiomer.
Dextrose is an aldohexose, levulose is a ketohexose. They differ chemically much.

Anyway - it's good that we vape good old nicotine, not those bloody carbohydrates.

Wow! Thanks for correcting me on this one! I normally can pull things from memory well, but this one definitely got messed up, or else I was taught wrong. Or both. Was never much of a carbo chemist...

My description of nicotine's enantiomers should all be correct though. But I'm afraid there are those vaping carbohydrates trying to sweeten their juices. No harm to them, but their attys are probably not too happy about it.

Very refreshing to have someone correct my chemistry. Stick around, Old Chemist...you could be quite useful around here! :thumbs:
 

Old Chemist

Super Member
ECF Veteran
Dec 23, 2009
324
130
68
Poland
starychemik.wordpress.com
Wow! Thanks for correcting me on this one! I normally can pull things from memory well, but this one definitely got messed up, or else I was taught wrong. Or both. Was never much of a carbo chemist...
Well... in fact, carbohydrates are group of compounds most chemists don't like. Including myself, of course. I am (or rather was) a specialist in physical organic chemistry.

My description of nicotine's enantiomers should all be correct though.
Right... your description was absolutely perfect.

Very refreshing to have someone correct my chemistry. Stick around, Old Chemist...you could be quite useful around here! :thumbs:
I'll be there - it's a very nice place - lots of interesting ideas.
 
  • Like
Reactions: Mr.Mann

DVap

Nicotiana Alchemia
ECF Veteran
Verified Member
Aug 26, 2009
1,548
1,586
Wow! Thanks for correcting me on this one! I normally can pull things from memory well, but this one definitely got messed up, or else I was taught wrong. Or both. Was never much of a carbo chemist...

My description of nicotine's enantiomers should all be correct though. But I'm afraid there are those vaping carbohydrates trying to sweeten their juices. No harm to them, but their attys are probably not too happy about it.

Very refreshing to have someone correct my chemistry. Stick around, Old Chemist...you could be quite useful around here! :thumbs:

Actually, I was about to correct you on the post back when you made it, but the site was misbehaving with connection resets and I got fed up and decided that the pleasure of correcting you wasn't worth all the effort... glad to see someone else busted ya. ;)
 

zoiDman

My -0^10 = Nothing at All*
Supporting Member
ECF Veteran
Apr 16, 2010
41,314
1
83,837
So-Cal
Status
Not open for further replies.

Users who are viewing this thread